4-Amino-6-chloropyrimidine → N-(6-Chloro-4-pyrimidyl)-4-hydroxy-2-methyl-2H-naphtho[2,1-e]-1,2-thiazine-3-carboxamide-1,1-dioxide

HRID 1730546Notes

Reaction equation

HRID 1730546 reaction equation
C[O:2][C:3]([C:5]1[N:6]([CH3:22])[S:7](=[O:21])(=[O:20])[C:8]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=[CH:12][C:9]=2[C:10]=1[OH:11])=O.[NH2:23][C:24]1[CH:29]=[C:28]([Cl:30])[N:27]=[CH:26][N:25]=1>C1(C)C(C)=CC=CC=1>[Cl:30][C:28]1[N:27]=[CH:26][N:25]=[C:24]([NH:23][C:3]([C:5]2[N:6]([CH3:22])[S:7](=[O:21])(=[O:20])[C:8]3[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[CH:13]=[CH:12][C:9]=3[C:10]=2[OH:11])=[O:2])[CH:29]=1

Participants

4

Reactant 2

HCID 2380124-Amino-6-chloropyrimidineHCID 546906514-hydroxy-2-methyl-2H-naphtho[2,1-e]-1,2-thiazine-3-carboxylic acid methylester-1,1-dioxide

Product 1

HCID 54695919N-(6-Chloro-4-pyrimidyl)-4-hydroxy-2-methyl-2H-naphtho[2,1-e]-1,2-thiazine-3-carboxamide-1,1-dioxideYield 47%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

N-(6-Chloro-4-pyrimidinyl)-4-hydroxy-2-methyl-2H-naphtho[2,1-e]-1,2-thiazine-3-carboxamide-1,1-dioxide was prepared analogous to Example 1 from 4-hydroxy-2-methyl-2H-naphtho[2,1-e]-1,2-thiazine-3-carboxylic acid methylester-1,1-dioxide and 4-amino-6-chloro-pyrimidine. Yield: 47% of theory; m.p. 263° C (decomp.; from xylene).

Sources & evidence

ORD record
ord-1220e706d60e476c9370283aef9ac5c5
Source dataset
uspto-grants-1976_11
Patent number
US03992535

Reaction notes

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