Methyl (R)-6-(bromomethyl)-4-(2-chloro-4-fluorophenyl)-2-(thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylate → HCID 86292123, compound

HRID 1778525Notes

Reaction equation

HRID 1778525 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C@H:6]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=2[Cl:25])[N:7]=[C:8]([C:13]2[S:14][CH:15]=[CH:16][N:17]=2)[NH:9][C:10]=1[CH2:11]Br)=[O:4].[F:26][C:27]1([F:35])[CH2:33][CH:32]2[NH:34][CH:28]1[CH2:29][O:30][CH2:31]2>>[Cl:25][C:19]1[CH:20]=[C:21]([F:24])[CH:22]=[CH:23][C:18]=1[C@H:6]1[C:5]([C:3]([O:2][CH3:1])=[O:4])=[C:10]([CH2:11][N:34]2[CH:28]3[C:27]([F:35])([F:26])[CH2:33][CH:32]2[CH2:31][O:30][CH2:29]3)[NH:9][C:8]([C:13]2[S:14][CH:15]=[CH:16][N:17]=2)=[N:7]1

Participants

3

Reactant 2

HCID 89995948Methyl (R)-6-(bromomethyl)-4-(2-chloro-4-fluorophenyl)-2-(thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylate2×HCID 117698181HCID 117698181, compound

Product 1

HCID 86292123HCID 86292123, compoundYield 5.2%

Procedure

The title compound was prepared in analogy to Example 1a in Scheme 3 by using methyl (4R)-4-(2-chloro-4-fluoro-phenyl)-6-(bromomethyl)-2-thiazol-2-yl-1,4-dihydropyrimidine-5-carboxylate (compound C, 100 mg) and 6,6-difluoro-3-oxa-8-azabicyclo[3.2.1]octane 108a (200 mg). 6 mg of the title compound was isolated as yellow powder.

Workup

  1. customThe title compound was prepared in analogy to Example 1a in Scheme 3

Sources & evidence

ORD record
ord-91ab272968c541cb9b561243908da7aa
Source dataset
uspto-grants-2016_02
Patent number
US09266904B2

Reaction notes

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