1-Methylimidazole → 4-(3-Chloro-4-methoxybenzylamino)-5-[(hydroxy)(1-methyl-2-imidazolyl)methyl]-2-methylthiopyrimidine

HRID 917598Notes

Reaction equation

HRID 917598 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][C:19]=1[O:20][CH3:21])[CH2:5][NH:6][C:7]1[C:12]([CH:13]=[O:14])=[CH:11][N:10]=[C:9]([S:15][CH3:16])[N:8]=1.[Li].[CH3:23][N:24]1[CH:28]=[CH:27][N:26]=[CH:25]1>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][C:19]=1[O:20][CH3:21])[CH2:5][NH:6][C:7]1[C:12]([CH:13]([OH:14])[C:25]2[N:24]([CH3:23])[CH:28]=[CH:27][N:26]=2)=[CH:11][N:10]=[C:9]([S:15][CH3:16])[N:8]=1

Participants

5

Reactant 3

HCID 13901-MethylimidazoleHCID 3028194LithiumHCID 220259362-Methylthio-4-(3-chloro-4-methoxybenzylamino)-5-formylpyrimidine

Product 1

HCID 220259064-(3-Chloro-4-methoxybenzylamino)-5-[(hydroxy)(1-methyl-2-imidazolyl)methyl]-2-methylthiopyrimidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-(3-chloro-4-methoxybenzylamino)-5-formyl-2-methylthiopyrimidine 0.5 g in tetrahydrofuran 20 ml is reacted at −78° C. with lithium salt of 1-methylimidazole 0.394 ml in the same manner as Example 86 to give 4-(3-chloro-4-methoxybenzylamino)-5-[(hydroxy) (1-methyl-2-imidazolyl)methyl]-2-methylthiopyrimidine. Thus obtained compound is oxidized at room temperature with manganese dioxide in chloroform and then the oxidized compound is post-treated in the same manner as Example 86 to give 4-(3-chloro-4-methoxybenzylamino)-5-(1-methyl-2-imidazolylcarbonyl-2-methylthiopyrimidine 0.5913 g. mp 158-159° C.

Sources & evidence

ORD record
ord-6a438c8aac1e43c48a4dfa4840d6a8cb
Source dataset
uspto-grants-2007_09
Patent number
US07273868B2

Reaction notes

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