Dimethylcarbamoyl Chloride → HCID 11583282, compound

HRID 1091404Notes

Reaction equation

[CH3:1][N:2]([CH3:6])[C:3](Cl)=[O:4].[NH2:7][C:8]1[CH:13]=[CH:12][C:11]([C@@H:14]2[O:19][CH2:18][CH2:17][N:16]([C:20]3[N:25]([CH3:26])[C:24](=[O:27])[CH:23]=[C:22]([C:28]4[CH:33]=[CH:32][N:31]=[CH:30][C:29]=4[F:34])[N:21]=3)[CH2:15]2)=[CH:10][CH:9]=1.C(N(CC)CC)C>O1CCCC1>[F:34][C:29]1[CH:30]=[N:31][CH:32]=[CH:33][C:28]=1[C:22]1[N:21]=[C:20]([N:16]2[CH2:17][CH2:18][O:19][C@@H:14]([C:11]3[CH:12]=[CH:13][C:8]([NH:7][C:3](=[O:4])[N:2]([CH3:6])[CH3:1])=[CH:9][CH:10]=3)[CH2:15]2)[N:25]([CH3:26])[C:24](=[O:27])[CH:23]=1

Participants

Conditions

Temperature: 50 °C

Procedure

N,N-Dimethylcarbamoyl chloride (0.26 g, 2.41 mmol) was added to a solution of 2-((2S)-2-(4-aminophenyl)morpholine-4-yl)-3-methyl-6-(3-fluoropyridin-4-yl)-3H-pyrimidin-4-one (0.45 g, 1.18 mmol) and triethylamine (1.2 g, 11.9 mmol) in tetrahydrofuran (20 ml) and the solution was stirred at 50° C. for 48 hours. The mixture was partitioned between water and chloroform. The organic layer was washed with brine, dried over magnesium sulfate, and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting 5-10% methanol in chloroform to furnish N′-(4-((2S)-4-(6-(3-fluoropyridin-4-yl)-3-methyl-4-oxo-3H-pyrimidin-2-yl)morpholin-2-yl)phenyl)-N,N-dimethylurea (0.35 g, 67%) as white crystals.

Workup

customThe mixture was partitioned between water and chloroform
washThe organic layer was washed with brine
dry with materialdried over magnesium sulfate
concentrationconcentrated in vacuo
customThe residue was purified by silica gel column chromatography
washeluting 5-10% methanol in chloroform

Sources & evidence

ORD record: ord-dea2076b744c4041a5428b08c861c96d
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08129377B2

Reaction notes

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