4-Methoxy-2-pyrimidinamine → tert-butyl N-[1-[4-(7-oxo-3-phenyl-1H-imidazo[1,2-a]pyrimidin-2-yl)phenyl]cyclobutyl]carbamate

HRID 872297

Reaction equation

HRID 872297 reaction equation
[C:1]([O:5][C:6](=[O:28])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18](=O)[CH:19](Br)[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C[O:30][C:31]1[CH:36]=[CH:35][N:34]=[C:33]([NH2:37])[N:32]=1>CN(C=O)C>[C:1]([O:5][C:6](=[O:28])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[N:37]=[C:33]4[N:32]=[C:31]([OH:30])[CH:36]=[CH:35][N:34]4[C:19]=3[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)=[CH:14][CH:13]=2)[CH2:9][CH2:10][CH2:11]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 674284-Methoxy-2-pyrimidinamineHCID 86691038tert-Butyl (1-{4-[bromo(phenyl)acetyl]phenyl}cyclobutyl)carbamate

Product 1

HCID 178452600tert-butyl N-[1-[4-(7-oxo-3-phenyl-1H-imidazo[1,2-a]pyrimidin-2-yl)phenyl]cyclobutyl]carbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of crude {1-[4-(2-bromo-2-phenyl-acetyl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester [Int-1-A] (1.26 g) and 4-methoxypyrimidin-2-ylamine (0.67 g) in DMF (21 mL) was heated overnight at 90° C. (bath temperature). On cooling the mixture was partitioned between EtOAc and water and the organic phase washed with brine, dried and concentrated to give a mixture of the title compound and Int-2-0. Purification was achieved by preparative HPLC to give the title compound.

Workup

  1. temperatureOn cooling the mixture
  2. customwas partitioned between EtOAc and water
  3. washthe organic phase washed with brine
  4. customdried
  5. concentrationconcentrated
  6. customto give

Sources & evidence

ORD record
ord-f7044b18d69d4fd0b4a5a19715df59e5
Source dataset
uspto-grants-2015_03
Patent number
US08975265B2

Linked notes

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