Water → HCID 67282022, compound

HRID 515479Notes

Reaction equation

HRID 515479 reaction equation
Cl.[Br:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[O:15][CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[CH:5][CH:4]=1.Cl[C:17]1[N:22]([CH3:23])[C:21](=[O:24])[CH:20]=[C:19]([C:25]2[CH:30]=[CH:29][N:28]=[CH:27][N:26]=2)[N:18]=1.C(N(CC)CC)C.O>O1CCCC1.C(Cl)(Cl)Cl>[Br:2][C:3]1[CH:4]=[CH:5][C:6]([CH:9]2[O:15][CH2:14][CH2:13][N:12]([C:17]3[N:22]([CH3:23])[C:21](=[O:24])[CH:20]=[C:19]([C:25]4[CH:30]=[CH:29][N:28]=[CH:27][N:26]=4)[N:18]=3)[CH2:11][CH2:10]2)=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 179544602-Chloro-3-methyl-6-(pyrimidin-4-YL)pyrimidin-4-oneHCID 66718576HCID 66718576, compound

Product 1

HCID 67282022HCID 67282022, compoundYield 76.7%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of optically active 7-(4-bromo-phenyl)-[1,4]oxazepane hydrochloride (0.10 g, 0.34 mmol) and 2-chloro-3-methyl-6-(pyrimidin-4-yl)-3H-pyrimidin-4-one (0.07 g, 0.30 mmol) in tetrahydrofuran (2 mL) was added triethylamine (0.08 mL), 0.60 mmol) at room temperature. The resulting mixture was stirred over night and poured into water. Extractive workup with chloroform was performed and the organic layer was dried over anhydrous sodium sulfate and concentrated. The residue was purified by recrystallization from ethyl acetate and diisopropyl ether to yield (+)-2-[7-(4-bromophenyl)-[1,4]-oxazepane-4-yl]-3-methyl-6-pyrimidin-4-yl-3H-pyrimidin-4-one (A096) (0.10 g, 0.23 mmol, 75%) as a white solid.

Workup

  1. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  2. concentrationconcentrated
  3. customThe residue was purified by recrystallization from ethyl acetate and diisopropyl ether

Sources & evidence

ORD record
ord-e4e04121206945ea894131415c5b1c95
Source dataset
uspto-grants-2015_08
Patent number
US09108957B2

Reaction notes

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