2-Bromopyrimidine → HCID 86588609, compound

HRID 2416738Notes

Reaction equation

HRID 2416738 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:33]=[CH:32][C:9]2[CH2:10][C@@H:11]([CH2:27][C:28]([O:30][CH3:31])=[O:29])[C:12](=[O:26])[N:13]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=3)[CH2:14][C:8]=2[CH:7]=1.Br[C:35]1[N:40]=[CH:39][CH:38]=[CH:37][N:36]=1.C(N(C(C)C)CC)(C)C>CN(C=O)C>[O:26]=[C:12]1[C@H:11]([CH2:27][C:28]([O:30][CH3:31])=[O:29])[CH2:10][C:9]2[CH:32]=[CH:33][C:6]([O:5][CH2:4][CH2:3][CH2:2][NH:1][C:35]3[N:40]=[CH:39][CH:38]=[CH:37][N:36]=3)=[CH:7][C:8]=2[CH2:14][N:13]1[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 783452-BromopyrimidineHCID 81531DiisopropylethylamineHCID 86588608HCID 86588608, compound

Product 1

HCID 86588609HCID 86588609, compoundYield 40.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of methyl (S)-8-(3-amino-1-propyloxy)-3-oxo-2-[4-(trifluoromethyl)benzyl]-2,3,4,5-tetrahydro-1H-2-benzazepine-4-acetate (0.09 g, 0.19 mmol), 2-bromopyrimidine (0.09 g, 0.57 mmol) and diisopropylethylamine (0.17 mL, 0.98 mmol) in DMF (2 mL) was heated at 80° C. for 18 h. The reaction was allowed to cool to RT and was concentrated to give a yellow residue. Flash chromatography on silica gel (2% MeOH/EtOAc) gave the title compound (42 mg) as a clear oil. MS (ES) m/e 543.1 (M+H)+.

Workup

  1. concentrationwas concentrated
  2. customto give a yellow residue

Sources & evidence

ORD record
ord-aa4543a012914eceb9cea936963617ed
Source dataset
uspto-grants-2004_11
Patent number
US06825188B2

Reaction notes

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