Methyl Ethyl Ketone → HCID 71611464, compound

HRID 1774539Notes

Reaction equation

[CH:1]1([C:4]2[N:8]([CH2:9][C:10]3[C:15]([F:16])=[CH:14][C:13]([O:17][CH2:18][CH3:19])=[CH:12][C:11]=3[F:20])[N:7]=[C:6]([C:21]3[N:26]=[C:25]([NH:27][C:28]4[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=4)[C:24]([OH:34])=[CH:23][N:22]=3)[C:5]=2[CH3:35])[CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:43][CH2:44][N:45]([CH3:47])[CH3:46].CC(=O)CC>CN(C=O)C>[CH:1]1([C:4]2[N:8]([CH2:9][C:10]3[C:11]([F:20])=[CH:12][C:13]([O:17][CH2:18][CH3:19])=[CH:14][C:15]=3[F:16])[N:7]=[C:6]([C:21]3[N:26]=[C:25]([NH:27][C:28]4[CH:29]=[CH:30][N:31]=[CH:32][CH:33]=4)[C:24]([O:34][CH2:43][CH2:44][N:45]([CH3:47])[CH3:46])=[CH:23][N:22]=3)[C:5]=2[CH3:35])[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 50 °C

Procedure

80 mg of 2-[5-cyclopropyl-1-(4-ethoxy-2,6-difluorobenzyl)-4-methyl-1H-pyrazol-3-yl]-4-(pyridin-4-ylamino)pyrimidin-5-ol 2-2-1 (0.048 mmol, 1.0 eq) were dissolved in 1.9 mL of dry DMF and 33.5 mg potassium carbonate (0.24 mmol, 5.0 eq) and 10.5 mg 2-chloro-N,N-dimethylethanamine (0.073 mmol, 1.5 eq) were added. The reaction mixture was stirred over night at 50° C. Then butan-2-one was added and the organic layer was washed with brine, dried over sodium sulfate and concentrated in vacuo. The purification of the residue by flash chromatography and HPLC provided 10 mg (0.02 mmol, 37%) of analytically pure target compound.

Workup

washthe organic layer was washed with brine
dry with materialdried over sodium sulfate
concentrationconcentrated in vacuo
customThe purification of the residue by flash chromatography and HPLC
customprovided 10 mg (0.02 mmol, 37%) of analytically pure target compound

Sources & evidence

ORD record: ord-a5baeca55a7c41d3a8236d49c02f6ef7
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09260412B2

Reaction notes

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