Ethyl Acetoacetate → Ethyl (S)-6-(bromomethyl)-4-(3-fluoro-2-methylphenyl)-2-(thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylate

HRID 590577Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[C@H](C2C=CC(F)=CC=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].[CH3:26][C:27]1[C:34]([F:35])=[CH:33][CH:32]=[CH:31][C:28]=1[CH:29]=O.[C:36](OCC)(=O)CC(C)=O>>[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][C@@H:29]([C:28]2[CH:31]=[CH:32][CH:33]=[C:34]([F:35])[C:27]=2[CH3:26])[C:5]=1[C:3]([O:2][CH2:1][CH3:36])=[O:4]

Participants

Reactant 3

HCID 8868Ethyl Acetoacetate

HCID 27792353-Fluoro-2-methylbenzaldehyde

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

Product 1

HCID 118358767Ethyl (S)-6-(bromomethyl)-4-(3-fluoro-2-methylphenyl)-2-(thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylate

Procedure

Compound C-3 was prepared in analogy to compound C by using 2-methyl-3-fluorobenzaldehyde instead of 2-chloro-4-fluorobenzaldehyde and ethyl acetoacetate instead of methyl acetoacetate.

Sources & evidence

ORD record: ord-0fba235a6d9d44e29861ab470667fefb
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09233978B2

Reaction notes

Loading…