Methylamine → 6-(N-Methylcarbamoyl)-2-{2-[3-(pyrid-2-yl)isoxazol-5-yl]pyrrolidin-1-yl]-4-(5-methyl-1H-pyrazol-3-ylamino)pyrimidine

HRID 2105203Notes

Reaction equation

C[O:2][C:3]([C:5]1[N:10]=[C:9]([N:11]2[CH2:15][CH2:14][CH2:13][CH:12]2[C:16]2[O:20][N:19]=[C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=3)[CH:17]=2)[N:8]=[C:7]([NH:27][C:28]2[CH:32]=[C:31]([CH3:33])[NH:30][N:29]=2)[CH:6]=1)=O.[CH3:34][NH2:35]>CO>[CH3:34][NH:35][C:3]([C:5]1[N:10]=[C:9]([N:11]2[CH2:15][CH2:14][CH2:13][CH:12]2[C:16]2[O:20][N:19]=[C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=3)[CH:17]=2)[N:8]=[C:7]([NH:27][C:28]2[CH:32]=[C:31]([CH3:33])[NH:30][N:29]=2)[CH:6]=1)=[O:2]

Participants

Conditions

Temperature: 65 °C

Procedure

A mixture of 6-methoxycarbonyl-2-{2-[3-(pyrid-2-yl)isoxazol-5-yl]pyrrolidin-1-yl}-4-(5-methyl-1H-pyrazol-3-ylamino)pyrimidine Example 56) (62.5 mg, 0.14 mmol), 2N solution of methylamine in methanol (2.0 ml, 4.00 mmol) and methanol (3.0 ml) was heated at 65° C. for 1 hour under microwave irradiation. The volatiles were removed by evaporation and the residue dissolved in DCM and purified by chromatography on silica gel eluting with DCM/methanol (100:0 increasing in polarity to 90:10). The purified product was triturated with diethylether and the resulting solid collected by filtration to give the title compound (21 mg, 34%).

Workup

customThe volatiles were removed by evaporation
dissolutionthe residue dissolved in DCM
custompurified by chromatography on silica gel eluting with DCM/methanol (100:0 increasing in polarity to 90:10)
customThe purified product was triturated with diethylether
filtrationthe resulting solid collected by filtration

Sources & evidence

ORD record: ord-cc4e86350d23489e8251af4a53060e6f
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07579349B2

Reaction notes

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