KR880009029A - Method for preparing pyrimido [5,4-b] [1,4] oxazine derivatives - Google Patents

Abstract

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Description

Method for preparing pyrimido [5,4-b] [1,4] oxazine derivatives

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Claims (1)

A method for producing a novel pyrimido [5,4-b] [1,4] oxazine derivative of the following structural formula (I), a tautomer thereof, a tautomeric mixture thereof and an acid addition salt thereof by the following method. Wherein R ¹ is a C _1-4 alkyl group: R ² is hydrogen or halogen or azido or -NR ⁵ R ⁶ , wherein ⁵ is hydrogen; Benzyl; A C _1-4 alkyl group unsubstituted or substituted with a hydroxyl group, R ⁶ is hydrogen; Or amino group; Or a C _3-6 cycloalkyl group; Or a straight or branched C _1-4 alkyl group optionally substituted with a hydroxyl, mercapto, amino carbonyl, furyl, 2-benzo [1,4] dioxanyl or di (C _1-4 alkyl) amino group ; Or a straight or branched C _1-4 alkyl group optionally substituted with a single or multiple substituted or unsubstituted phenyl group or phenoxy group with halogen or C _1-4 alkoxy group (s); Or a straight or branched C _1-4 alkyl group optionally containing further nitrogen or oxygen atoms, optionally substituted with a C _1-4 alkyl or benzyl group optionally substituted with a nitrogen-containing 6-membered saturated heterocycle; ; Or NR ⁵ R ⁶ optionally further comprises no or no nitrogen or oxygen atoms and is a nitrogen-containing 6-membered saturated heterocycle optionally unsubstituted or substituted with a C _2-4 alkoxycarbonyl or C _1-4 hydroxyalkyl group. R ³ and R ⁴ are the same as or different from each other, and are hydrogen or a C _1-4 alkyl group; R ⁹ is “R ² is not chlorine, 4-morpholinyl group and piperidyl group when R ⁹ is hydrogen, or R ² is not chlorine and 4-morpholinyl group when R ⁹ is methyl or benzyl group” Under the condition that R ⁹ is hydrogen; Or an unsubstituted C _1-4 alkyl group; Or a C _1-4 alkyl group single or polysubstituted with an oxo, cyano, aminocarbonyl, C _2-5 alkoxycarbonyl, pyridyl, morpholinocarbonyl, hydroxyl or phenyl group. a) the compound of formula (II) Wherein R ¹ , R ³ , R ⁴ and R ⁹ are as described above for formula (I) and R ¹⁰ is a leaving group. Is reacted with an amine of the formula -HNR ⁵ R ⁶ (optionally having a protecting group, R ⁵ and R ⁶ as described above for structure (I)), wherein formula (I) (R ² is -NR ⁵ R ⁶ Wherein R ⁵ and R ⁶ are as described above and R ¹ , R ³ , R ⁴ and R ⁹ are as described above); b) diazotizing the compound of formula (I) (R ¹ , R ³ , R ⁴ and R ⁹ are as described above for formula (I), and R ² is a hydrazino group) In which R ² is an azido group and R ¹ , R ³ , R ⁴ and R ⁹ are as described above); c) reacting a compound of formula (I), wherein R ¹ , R ² , R ³ and R ⁴ are as described above for formula (I), wherein R ⁹ is hydrogen, with 2,3-epoxy propanol Preparing a compound of formula (I) wherein R ¹ , R ² , R ³ and R ⁴ are as defined above and R ⁹ is a 2,3-dihydroxypropyl group; Formula (I), optionally having a protecting group, prepared in step a) or b) above, wherein R ¹ , R ² , R ³ and R ⁴ are as described above for formula (I), and R ⁹ is hydrogen ) Is reacted with a compound of formula R ⁹ X (optionally having a protecting group, R ⁹ is as described above for formula (I) except hydrogen, X is a leaving group); And / or removing the protecting group from the product prepared by any of the processes a) -c) above; And / or converting the compound of formula (I) prepared by the above-mentioned method into another compound of formula (I); And / or the base of formula (I) prepared by the method described above is converted to an acid addition salt by reacting with an acid; And / or converting acid addition salts to other types of acid addition salts; And / or liberating the base of formula (I) from an acid addition salt to prepare a compound of formula (I), a tautomer thereof, a tautomeric mixture thereof or an acid addition salt thereof. ※ Note: The disclosure is based on the initial application.