4-Chlorobenzaldehyde → Methyl 6-(bromomethyl)-4-(4-chlorophenyl)-1,4-dihydro-2-(2-thiazolyl)-5-pyrimidinecarboxylate

HRID 590578Notes

Reaction equation

HRID 590578 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C@H:6]([C:18]2[CH:23]=[CH:22][C:21](F)=[CH:20][C:19]=2Cl)[N:7]=[C:8]([C:13]2[S:14][CH:15]=[CH:16][N:17]=2)[NH:9][C:10]=1[CH2:11][Br:12])=[O:4].[Cl:26]C1C=CC(C=O)=CC=1>>[Br:12][CH2:11][C:10]1[NH:9][C:8]([C:13]2[S:14][CH:15]=[CH:16][N:17]=2)=[N:7][CH:6]([C:18]2[CH:23]=[CH:22][C:21]([Cl:26])=[CH:20][CH:19]=2)[C:5]=1[C:3]([O:2][CH3:1])=[O:4]

Participants

3

Reactant 2

HCID 77264-ChlorobenzaldehydeHCID 89995948Methyl (R)-6-(bromomethyl)-4-(2-chloro-4-fluorophenyl)-2-(thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylate

Product 1

HCID 118354471Methyl 6-(bromomethyl)-4-(4-chlorophenyl)-1,4-dihydro-2-(2-thiazolyl)-5-pyrimidinecarboxylate

Procedure

Compound C-4 was prepared in analogy to compound C by using 4-chlorobenzaldehyde instead of 2-chloro-4-fluorobenzaldehyde without chiral SFC separation of dihydropyrimidine intermediate in Scheme 1-1.

Workup

  1. customwithout chiral SFC separation of dihydropyrimidine intermediate in Scheme 1-1

Sources & evidence

ORD record
ord-9099d8814c304b46826590804ac38ebe
Source dataset
uspto-grants-2016_01
Patent number
US09233978B2

Reaction notes

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