Dimethylcarbamoyl Chloride → 1,1-Dimethyl-3-{4-[4-(1-methyl-6-oxo-4-pyridin-4-yl-1,6-dihydro-pyrimidin-2-yl) morpholin-2-yl]-phenyl}-urea

HRID 424447Notes

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][CH:29]=4)[N:21]=3)[CH2:15]2)=[CH:10][CH:9]=1.C(N(CC)CC)C>O1CCCC1>[CH3:1][N:2]([CH3:6])[C:3]([NH:7][C:8]1[CH:9]=[CH:10][C:11]([CH: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:29]=[CH:30][N:31]=[CH:32][CH:33]=4)[N:21]=3)[CH2:15]2)=[CH:12][CH:13]=1)=[O:4]

Participants

Conditions

Temperature: 50 °C

Procedure

N,N-Dimethylcarbamoyl chloride (0.24 g, 2.23 mmol) was added to a solution of 2-[(2S)-2-(4-aminophenyl)morpholin-4-yl]-3-methyl-6-(pyridin-4-yl)-pyrimidin-4(3H)-one (0.40 g, 1.10 mmol) and triethylamine (1.1 g, 10.9 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 chromatography eluting 5-10% methanol in chloroform to furnish 1,1-Dimethyl-3-{4-[4-(1-methyl-6-oxo-4-pyridin-4-yl-1,6-dihydro-pyrimidin-2-yl) morpholin-2-yl]-phenyl}-urea (0.14 g, 30%) 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 chromatography
washeluting 5-10% methanol in chloroform

Sources & evidence

ORD record: ord-fddca55455b24d1b86d1c2bcd3d0c1b9
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08106045B2

Reaction notes

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