Potassium Carbonate → HCID 117697538, compound

HRID 1778537Notes

Reaction equation

HRID 1778537 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@H:9]1[C:14]([C:15]([O-:17])=[O:16])=[C:13]([CH2:18]Br)[NH:12][C:11]([C:20]2[S:21][CH:22]=[CH:23][N:24]=2)=[N:10]1.[CH:25]12[NH:32][CH:29]([CH2:30][CH2:31]1)[CH2:28][N:27]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:26]2.[C:40](=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@H:9]1[C:14]([C:15]([O:17][CH3:40])=[O:16])=[C:13]([CH2:18][N:32]2[CH:29]3[CH2:30][CH2:31][CH:25]2[CH2:26][N:27]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:28]3)[NH:12][C:11]([C:20]2[S:21][CH:22]=[CH:23][N:24]=2)=[N:10]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 21904757tert-Butyl 3,8-diazabicyclo[3.2.1]octane-3-carboxylateHCID 131734826(4R)-4-(2-chloro-4-fluoro-phenyl)-6-(bromomethyl)-2-thiazol-2-yl-1,4-dihydropyrimidine-5-carboxylate2×

Product 1

HCID 117697538HCID 117697538, compoundYield 106.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl (4R)-6-(bromomethyl)-4-(2-chloro-4-fluoro-phenyl)-2-thiazol-2-yl-1,4-dihydropyrimidine-5-carboxylate (compound C, 80 mg, 0.13 mmol) in dimethylformamide (3.0 mL) was added compound tert-butyl 3,8-diazabicyclo[3.2.1]octane-3-carboxylate (28 mg, 0.13 mmol) and potassium carbonate (40 mg, 0.29 mmol). The reaction mixture was stirred at room temperature overnight. The reaction mixture was poured into ice-water, extracted with EA (20 mL) three times. The combined organic phase was concentrated to give a crude tert-butyl 8-[[(4R)-4-(2-chloro-4-fluoro-phenyl)-5-methoxycarbonyl-2-thiazol-2-yl-1,4-dihydropyrimidin-6-yl]methyl]-3,8-diazabicyclo[3.2.1]octane-3-carboxylate (80 mg).

Workup

  1. extractionextracted with EA (20 mL) three times
  2. concentrationThe combined organic phase was concentrated

Sources & evidence

ORD record
ord-38cd8ee081674175befe381be27a260b
Source dataset
uspto-grants-2016_02
Patent number
US09266904B2

Reaction notes

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