JP4405593B2 - チエノピリミジン類 - Google Patents

Info

Publication number

JP4405593B2

JP4405593B2 JP50934398A JP50934398A JP4405593B2 JP 4405593 B2 JP4405593 B2 JP 4405593B2 JP 50934398 A JP50934398 A JP 50934398A JP 50934398 A JP50934398 A JP 50934398A JP 4405593 B2 JP4405593 B2 JP 4405593B2

Authority

JP

Japan

Prior art keywords

pyrimidine

chloro

pyridin

reacting

thieno

Prior art date

1996-08-12

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Expired - Fee Related

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• -1 1-imidazolyl Chemical group 0.000 claims description 155
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 46
• 150000001875 compounds Chemical class 0.000 claims description 46
• 125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 claims description 25
• 150000003839 salts Chemical class 0.000 claims description 20
• 125000004432 carbon atom Chemical group C* 0.000 claims description 15
• 238000000034 method Methods 0.000 claims description 11
• 239000002253 acid Substances 0.000 claims description 10
• 125000000623 heterocyclic group Chemical group 0.000 claims description 8
• LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 7
• 125000002947 alkylene group Chemical group 0.000 claims description 6
• 238000002360 preparation method Methods 0.000 claims description 6
• 125000000217 alkyl group Chemical group 0.000 claims description 5
• 238000004519 manufacturing process Methods 0.000 claims description 5
• 229910052760 oxygen Inorganic materials 0.000 claims description 4
• 229910052717 sulfur Inorganic materials 0.000 claims description 4
• 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 3
• 150000007514 bases Chemical class 0.000 claims description 2
• 229910052799 carbon Inorganic materials 0.000 claims description 2
• HDNPFZFZOMWGKL-UHFFFAOYSA-N n-(1,3-benzodioxol-5-ylmethyl)-2-imidazol-1-yl-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidin-4-amine Chemical compound C=1C=C2OCOC2=CC=1CNC(C=1C=2CCCCC=2SC=1N=1)=NC=1N1C=CN=C1 HDNPFZFZOMWGKL-UHFFFAOYSA-N 0.000 claims description 2
• ZAXMDLTUPHLTQX-UHFFFAOYSA-N n-(1,3-benzodioxol-5-ylmethyl)-2-imidazol-1-yl-5,6-dimethylthieno[2,3-d]pyrimidin-4-amine Chemical compound N=1C(NCC=2C=C3OCOC3=CC=2)=C2C(C)=C(C)SC2=NC=1N1C=CN=C1 ZAXMDLTUPHLTQX-UHFFFAOYSA-N 0.000 claims description 2
• YHXMDXMNJHOQDN-UHFFFAOYSA-N n-(1,3-benzodioxol-5-ylmethyl)-2-pyridin-3-yl-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidin-4-amine Chemical compound C=1C=C2OCOC2=CC=1CNC(C=1C=2CCCCC=2SC=1N=1)=NC=1C1=CC=CN=C1 YHXMDXMNJHOQDN-UHFFFAOYSA-N 0.000 claims description 2
• 229910052757 nitrogen Inorganic materials 0.000 claims description 2
• 125000005279 aryl sulfonyloxy group Chemical group 0.000 claims 2
• 125000003226 pyrazolyl group Chemical group 0.000 claims 1
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 237
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 47
• 125000004499 isoxazol-5-yl group Chemical group O1N=CC=C1* 0.000 description 46
• 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 45
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 44
• 238000006243 chemical reaction Methods 0.000 description 34
• 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 description 24
• 125000004353 pyrazol-1-yl group Chemical group [H]C1=NN(*)C([H])=C1[H] 0.000 description 20
• VCJCJLZVNOZZLS-UHFFFAOYSA-N [1]benzothiolo[2,3-d]pyrimidine Chemical compound C1=NC=C2C3=CC=CC=C3SC2=N1 VCJCJLZVNOZZLS-UHFFFAOYSA-N 0.000 description 18
• 239000004480 active ingredient Substances 0.000 description 15
• OTIFYNRGBHJTIF-UHFFFAOYSA-N 4-chloro-6-ethyl-2-pyridin-3-ylthieno[2,3-d]pyrimidine Chemical compound N1=C2SC(CC)=CC2=C(Cl)N=C1C1=CC=CN=C1 OTIFYNRGBHJTIF-UHFFFAOYSA-N 0.000 description 12
• PBYXYXCGKUOTBM-UHFFFAOYSA-N 4-chloro-6-methyl-2-pyrazin-2-ylthieno[2,3-d]pyrimidine Chemical compound N1=C2SC(C)=CC2=C(Cl)N=C1C1=CN=CC=N1 PBYXYXCGKUOTBM-UHFFFAOYSA-N 0.000 description 12
• ORKQHNXBQXVUTL-UHFFFAOYSA-N 4-chloro-6-methyl-2-pyridin-2-ylthieno[2,3-d]pyrimidine Chemical compound N1=C2SC(C)=CC2=C(Cl)N=C1C1=CC=CC=N1 ORKQHNXBQXVUTL-UHFFFAOYSA-N 0.000 description 12
• GULXKZDMNVVRDB-UHFFFAOYSA-N 5-(4-chloro-6-methylthieno[2,3-d]pyrimidin-2-yl)-1,2-oxazole Chemical compound N1=C2SC(C)=CC2=C(Cl)N=C1C1=CC=NO1 GULXKZDMNVVRDB-UHFFFAOYSA-N 0.000 description 12
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
• MWCLMVSZYQJPRH-UHFFFAOYSA-N 4,5-dichloro-6-methyl-2-pyrazin-2-ylthieno[2,3-d]pyrimidine Chemical compound N=1C(Cl)=C2C(Cl)=C(C)SC2=NC=1C1=CN=CC=N1 MWCLMVSZYQJPRH-UHFFFAOYSA-N 0.000 description 11
• VSDJNTVDUJGCIG-UHFFFAOYSA-N 4,5-dichloro-6-methyl-2-pyridin-2-ylthieno[2,3-d]pyrimidine Chemical compound N=1C(Cl)=C2C(Cl)=C(C)SC2=NC=1C1=CC=CC=N1 VSDJNTVDUJGCIG-UHFFFAOYSA-N 0.000 description 11
• YXZIQOHVSRAWKC-UHFFFAOYSA-N 4,5-dichloro-6-methyl-2-pyridin-4-ylthieno[2,3-d]pyrimidine Chemical compound N=1C(Cl)=C2C(Cl)=C(C)SC2=NC=1C1=CC=NC=C1 YXZIQOHVSRAWKC-UHFFFAOYSA-N 0.000 description 11
• ZAHZQWAXUPTDJE-UHFFFAOYSA-N 4,6-dichloro-2-pyrazin-2-ylthieno[2,3-d]pyrimidine Chemical compound N1=C2SC(Cl)=CC2=C(Cl)N=C1C1=CN=CC=N1 ZAHZQWAXUPTDJE-UHFFFAOYSA-N 0.000 description 11
• ZYRYAZJTWFMYGE-UHFFFAOYSA-N 4,6-dichloro-2-pyridin-2-ylthieno[2,3-d]pyrimidine Chemical compound N1=C2SC(Cl)=CC2=C(Cl)N=C1C1=CC=CC=N1 ZYRYAZJTWFMYGE-UHFFFAOYSA-N 0.000 description 11
• YKOYVPUMJJBMBP-UHFFFAOYSA-N 4,6-dichloro-2-pyridin-3-ylthieno[2,3-d]pyrimidine Chemical compound N1=C2SC(Cl)=CC2=C(Cl)N=C1C1=CC=CN=C1 YKOYVPUMJJBMBP-UHFFFAOYSA-N 0.000 description 11
• CFPMOZDJGLHGEP-UHFFFAOYSA-N 4,6-dichloro-2-pyridin-4-ylthieno[2,3-d]pyrimidine Chemical compound N1=C2SC(Cl)=CC2=C(Cl)N=C1C1=CC=NC=C1 CFPMOZDJGLHGEP-UHFFFAOYSA-N 0.000 description 11
• GEPPWBCPYIBEHQ-UHFFFAOYSA-N 4-chloro-2-pyrazin-2-yl-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidine Chemical compound N=1C=2SC=3CCCCC=3C=2C(Cl)=NC=1C1=CN=CC=N1 GEPPWBCPYIBEHQ-UHFFFAOYSA-N 0.000 description 11
• KLXAGVAFARUQRY-UHFFFAOYSA-N 4-chloro-2-pyrazin-2-yl-6-(trifluoromethyl)thieno[2,3-d]pyrimidine Chemical compound N1=C2SC(C(F)(F)F)=CC2=C(Cl)N=C1C1=CN=CC=N1 KLXAGVAFARUQRY-UHFFFAOYSA-N 0.000 description 11
• GTVYNNDHOKJILR-UHFFFAOYSA-N 4-chloro-2-pyridin-2-yl-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidine Chemical compound N=1C=2SC=3CCCCC=3C=2C(Cl)=NC=1C1=CC=CC=N1 GTVYNNDHOKJILR-UHFFFAOYSA-N 0.000 description 11
• IFISBEYDEGFLMI-UHFFFAOYSA-N 4-chloro-2-pyridin-2-yl-6-(trifluoromethyl)thieno[2,3-d]pyrimidine Chemical compound N1=C2SC(C(F)(F)F)=CC2=C(Cl)N=C1C1=CC=CC=N1 IFISBEYDEGFLMI-UHFFFAOYSA-N 0.000 description 11
• ISKGKMVCOYALTM-UHFFFAOYSA-N 4-chloro-2-pyridin-3-yl-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidine Chemical compound N=1C=2SC=3CCCCC=3C=2C(Cl)=NC=1C1=CC=CN=C1 ISKGKMVCOYALTM-UHFFFAOYSA-N 0.000 description 11
• NUUDPHDEZJUWDZ-UHFFFAOYSA-N 4-chloro-2-pyridin-3-yl-6-(trifluoromethyl)thieno[2,3-d]pyrimidine Chemical compound N1=C2SC(C(F)(F)F)=CC2=C(Cl)N=C1C1=CC=CN=C1 NUUDPHDEZJUWDZ-UHFFFAOYSA-N 0.000 description 11
• YYIQTSLTZZVFCK-UHFFFAOYSA-N 4-chloro-2-pyridin-4-yl-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidine Chemical compound N=1C=2SC=3CCCCC=3C=2C(Cl)=NC=1C1=CC=NC=C1 YYIQTSLTZZVFCK-UHFFFAOYSA-N 0.000 description 11
• RITRSKXLEDGLQP-UHFFFAOYSA-N 4-chloro-2-pyridin-4-yl-6-(trifluoromethyl)thieno[2,3-d]pyrimidine Chemical compound N1=C2SC(C(F)(F)F)=CC2=C(Cl)N=C1C1=CC=NC=C1 RITRSKXLEDGLQP-UHFFFAOYSA-N 0.000 description 11
• UUTZWNAQEFVRGF-UHFFFAOYSA-N 4-chloro-5,6-dimethyl-2-pyrazin-2-ylthieno[2,3-d]pyrimidine Chemical compound N=1C(Cl)=C2C(C)=C(C)SC2=NC=1C1=CN=CC=N1 UUTZWNAQEFVRGF-UHFFFAOYSA-N 0.000 description 11
• HCVJZEMOIVEUFU-UHFFFAOYSA-N 4-chloro-5,6-dimethyl-2-pyridin-2-ylthieno[2,3-d]pyrimidine Chemical compound N=1C(Cl)=C2C(C)=C(C)SC2=NC=1C1=CC=CC=N1 HCVJZEMOIVEUFU-UHFFFAOYSA-N 0.000 description 11
• OKMOUSJGXYXWHP-UHFFFAOYSA-N 4-chloro-5,6-dimethyl-2-pyridin-3-ylthieno[2,3-d]pyrimidine Chemical compound N=1C(Cl)=C2C(C)=C(C)SC2=NC=1C1=CC=CN=C1 OKMOUSJGXYXWHP-UHFFFAOYSA-N 0.000 description 11
• KHIFGUKETTZHOC-UHFFFAOYSA-N 4-chloro-5,6-dimethyl-2-pyridin-4-ylthieno[2,3-d]pyrimidine Chemical compound N=1C(Cl)=C2C(C)=C(C)SC2=NC=1C1=CC=NC=C1 KHIFGUKETTZHOC-UHFFFAOYSA-N 0.000 description 11
• FNXUGYJHBRERJW-UHFFFAOYSA-N 4-chloro-5-methyl-2-pyridin-2-ylthieno[2,3-d]pyrimidine Chemical compound N=1C(Cl)=C2C(C)=CSC2=NC=1C1=CC=CC=N1 FNXUGYJHBRERJW-UHFFFAOYSA-N 0.000 description 11
• YOGKDNQRONQSSZ-UHFFFAOYSA-N 4-chloro-5-methyl-2-pyridin-3-ylthieno[2,3-d]pyrimidine Chemical compound N=1C(Cl)=C2C(C)=CSC2=NC=1C1=CC=CN=C1 YOGKDNQRONQSSZ-UHFFFAOYSA-N 0.000 description 11
• YFTQPWJKANFRBY-UHFFFAOYSA-N 4-chloro-6-ethyl-2-pyrazin-2-ylthieno[2,3-d]pyrimidine Chemical compound N1=C2SC(CC)=CC2=C(Cl)N=C1C1=CN=CC=N1 YFTQPWJKANFRBY-UHFFFAOYSA-N 0.000 description 11
• MRYZQOMGKWXKKC-UHFFFAOYSA-N 4-chloro-6-ethyl-2-pyridin-2-ylthieno[2,3-d]pyrimidine Chemical compound N1=C2SC(CC)=CC2=C(Cl)N=C1C1=CC=CC=N1 MRYZQOMGKWXKKC-UHFFFAOYSA-N 0.000 description 11
• VROKTDMUCLPWTE-UHFFFAOYSA-N 4-chloro-6-ethyl-2-pyridin-4-ylthieno[2,3-d]pyrimidine Chemical compound N1=C2SC(CC)=CC2=C(Cl)N=C1C1=CC=NC=C1 VROKTDMUCLPWTE-UHFFFAOYSA-N 0.000 description 11
• CUURLLLXVGYGBR-UHFFFAOYSA-N 4-chloro-6-methyl-2-pyridin-3-ylthieno[2,3-d]pyrimidine Chemical compound N1=C2SC(C)=CC2=C(Cl)N=C1C1=CC=CN=C1 CUURLLLXVGYGBR-UHFFFAOYSA-N 0.000 description 11
• FCIHEKTYBKVMGN-UHFFFAOYSA-N 4-chloro-6-methyl-2-pyridin-4-ylthieno[2,3-d]pyrimidine Chemical compound N1=C2SC(C)=CC2=C(Cl)N=C1C1=CC=NC=C1 FCIHEKTYBKVMGN-UHFFFAOYSA-N 0.000 description 11
• CXZPHUKTMYBJLS-UHFFFAOYSA-N 4-chloro-6-nitro-2-pyrazin-2-ylthieno[2,3-d]pyrimidine Chemical compound N1=C2SC([N+](=O)[O-])=CC2=C(Cl)N=C1C1=CN=CC=N1 CXZPHUKTMYBJLS-UHFFFAOYSA-N 0.000 description 11
• ZFJKZWDYHJLWOS-UHFFFAOYSA-N 4-chloro-6-nitro-2-pyridin-3-ylthieno[2,3-d]pyrimidine Chemical compound N1=C2SC([N+](=O)[O-])=CC2=C(Cl)N=C1C1=CC=CN=C1 ZFJKZWDYHJLWOS-UHFFFAOYSA-N 0.000 description 11
• QNMXKWMTQYUFIP-UHFFFAOYSA-N 4-chloro-6-nitro-2-pyridin-4-ylthieno[2,3-d]pyrimidine Chemical compound N1=C2SC([N+](=O)[O-])=CC2=C(Cl)N=C1C1=CC=NC=C1 QNMXKWMTQYUFIP-UHFFFAOYSA-N 0.000 description 11
• JGSWNEJDONIMSQ-UHFFFAOYSA-N 5-(4,5-dichloro-6-methylthieno[2,3-d]pyrimidin-2-yl)-1,2-oxazole Chemical compound N=1C(Cl)=C2C(Cl)=C(C)SC2=NC=1C1=CC=NO1 JGSWNEJDONIMSQ-UHFFFAOYSA-N 0.000 description 11
• LQPGWPKTMQTYEG-UHFFFAOYSA-N 5-(4,6-dichlorothieno[2,3-d]pyrimidin-2-yl)-1,2-oxazole Chemical compound N1=C2SC(Cl)=CC2=C(Cl)N=C1C1=CC=NO1 LQPGWPKTMQTYEG-UHFFFAOYSA-N 0.000 description 11
• LDWOHYXTFVXIQS-UHFFFAOYSA-N 5-(4-chloro-6-nitrothieno[2,3-d]pyrimidin-2-yl)-1,2-oxazole Chemical compound N1=C2SC([N+](=O)[O-])=CC2=C(Cl)N=C1C1=CC=NO1 LDWOHYXTFVXIQS-UHFFFAOYSA-N 0.000 description 11
• QHFRZUWIJCIJFY-UHFFFAOYSA-N 5-[4-chloro-6-(trifluoromethyl)thieno[2,3-d]pyrimidin-2-yl]-1,2-oxazole Chemical compound N1=C2SC(C(F)(F)F)=CC2=C(Cl)N=C1C1=CC=NO1 QHFRZUWIJCIJFY-UHFFFAOYSA-N 0.000 description 11
• 239000000243 solution Substances 0.000 description 11
• QGACYODQBCOZNU-UHFFFAOYSA-N 4,5-dichloro-6-methyl-2-pyridin-3-ylthieno[2,3-d]pyrimidine Chemical compound N=1C(Cl)=C2C(Cl)=C(C)SC2=NC=1C1=CC=CN=C1 QGACYODQBCOZNU-UHFFFAOYSA-N 0.000 description 10
• WSHSXKLVAIQDHW-UHFFFAOYSA-N 4-chloro-5-methyl-2-pyridin-4-ylthieno[2,3-d]pyrimidine Chemical compound N=1C(Cl)=C2C(C)=CSC2=NC=1C1=CC=NC=C1 WSHSXKLVAIQDHW-UHFFFAOYSA-N 0.000 description 10
• NBVIHUXALANKGR-UHFFFAOYSA-N 4-chloro-6-nitro-2-pyridin-2-ylthieno[2,3-d]pyrimidine Chemical compound N1=C2SC([N+](=O)[O-])=CC2=C(Cl)N=C1C1=CC=CC=N1 NBVIHUXALANKGR-UHFFFAOYSA-N 0.000 description 10
• LZEXIGQJTPZXOJ-UHFFFAOYSA-N 5-(4-chloro-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidin-2-yl)-1,2-oxazole Chemical compound N=1C=2SC=3CCCCC=3C=2C(Cl)=NC=1C1=CC=NO1 LZEXIGQJTPZXOJ-UHFFFAOYSA-N 0.000 description 10
• IWTSZXCXPHRPCW-UHFFFAOYSA-N 5-(4-chloro-5,6-dimethylthieno[2,3-d]pyrimidin-2-yl)-1,2-oxazole Chemical compound N=1C(Cl)=C2C(C)=C(C)SC2=NC=1C1=CC=NO1 IWTSZXCXPHRPCW-UHFFFAOYSA-N 0.000 description 10
• USWGRWJYYZRROE-UHFFFAOYSA-N 5-(4-chloro-5-methylthieno[2,3-d]pyrimidin-2-yl)-1,2-oxazole Chemical compound N=1C(Cl)=C2C(C)=CSC2=NC=1C1=CC=NO1 USWGRWJYYZRROE-UHFFFAOYSA-N 0.000 description 10
• MWRFSEYWRUQNCH-UHFFFAOYSA-N 5-(4-chloro-6-ethylthieno[2,3-d]pyrimidin-2-yl)-1,2-oxazole Chemical compound N1=C2SC(CC)=CC2=C(Cl)N=C1C1=CC=NO1 MWRFSEYWRUQNCH-UHFFFAOYSA-N 0.000 description 10
• SMDKSCIOCNGNMJ-UHFFFAOYSA-N 2,4,5-trichloro-6-methylthieno[2,3-d]pyrimidine Chemical compound ClC1=NC(Cl)=C2C(Cl)=C(C)SC2=N1 SMDKSCIOCNGNMJ-UHFFFAOYSA-N 0.000 description 9
• XNAZNWXVGHIFTK-UHFFFAOYSA-N 2,4,6-trichlorothieno[2,3-d]pyrimidine Chemical compound N1=C(Cl)N=C2SC(Cl)=CC2=C1Cl XNAZNWXVGHIFTK-UHFFFAOYSA-N 0.000 description 9
• CPWQCJFDDILDOU-UHFFFAOYSA-N 2,4-dichloro-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidine Chemical compound C1CCCC2=C1C1=C(Cl)N=C(Cl)N=C1S2 CPWQCJFDDILDOU-UHFFFAOYSA-N 0.000 description 9
• LDXCWOSUWRNYEW-UHFFFAOYSA-N 2,4-dichloro-5,6-dimethylthieno[2,3-d]pyrimidine Chemical compound ClC1=NC(Cl)=C2C(C)=C(C)SC2=N1 LDXCWOSUWRNYEW-UHFFFAOYSA-N 0.000 description 9
• OIJVRHXVISHQPS-UHFFFAOYSA-N 2,4-dichloro-5-methylthieno[2,3-d]pyrimidine Chemical compound ClC1=NC(Cl)=C2C(C)=CSC2=N1 OIJVRHXVISHQPS-UHFFFAOYSA-N 0.000 description 9
• WILLJMUZTUFCPD-UHFFFAOYSA-N 2,4-dichloro-6-ethylthieno[2,3-d]pyrimidine Chemical compound N1=C(Cl)N=C2SC(CC)=CC2=C1Cl WILLJMUZTUFCPD-UHFFFAOYSA-N 0.000 description 9
• BTGNDWIMNVJZJY-UHFFFAOYSA-N 2,4-dichloro-6-methylthieno[2,3-d]pyrimidine Chemical compound N1=C(Cl)N=C2SC(C)=CC2=C1Cl BTGNDWIMNVJZJY-UHFFFAOYSA-N 0.000 description 9
• BCHQHHYTBVURCM-UHFFFAOYSA-N 2,4-dichloro-6-nitrothieno[2,3-d]pyrimidine Chemical compound N1=C(Cl)N=C2SC([N+](=O)[O-])=CC2=C1Cl BCHQHHYTBVURCM-UHFFFAOYSA-N 0.000 description 9
• LSFQLFVVDGXGTI-UHFFFAOYSA-N 4-chloro-5-methyl-2-pyrazin-2-ylthieno[2,3-d]pyrimidine Chemical compound N=1C(Cl)=C2C(C)=CSC2=NC=1C1=CN=CC=N1 LSFQLFVVDGXGTI-UHFFFAOYSA-N 0.000 description 9
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
• 238000002844 melting Methods 0.000 description 9
• 230000008018 melting Effects 0.000 description 9
• 239000000203 mixture Substances 0.000 description 9
• JIMQJLMPZVYOFI-UHFFFAOYSA-N 2,4-dichloro-6-(trifluoromethyl)thieno[2,3-d]pyrimidine Chemical compound N1=C(Cl)N=C2SC(C(F)(F)F)=CC2=C1Cl JIMQJLMPZVYOFI-UHFFFAOYSA-N 0.000 description 8
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Natural products CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
• 239000003814 drug Substances 0.000 description 7
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 7
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
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