Phenyl isocyanate → 1-[2-Methyl-4-[4-[(3S)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]phenyl]-3-phenyl-urea

HRID 2353628Notes

Reaction equation

[CH3:1][C:2]1[CH:8]=[C:7]([C:9]2[N:14]=[C:13]([N:15]3[CH2:20][CH2:19][O:18][CH2:17][C@@H:16]3[CH3:21])[CH:12]=[C:11]([CH2:22][S:23]([CH3:26])(=[O:25])=[O:24])[N:10]=2)[CH:6]=[CH:5][C:3]=1[NH2:4].[C:27]1([N:33]=[C:34]=[O:35])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>O1CCOCC1>[CH3:1][C:2]1[CH:8]=[C:7]([C:9]2[N:14]=[C:13]([N:15]3[CH2:20][CH2:19][O:18][CH2:17][C@@H:16]3[CH3:21])[CH:12]=[C:11]([CH2:22][S:23]([CH3:26])(=[O:25])=[O:24])[N:10]=2)[CH:6]=[CH:5][C:3]=1[NH:4][C:34]([NH:33][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:35]

Participants

Conditions

Temperature: 75 °C

Procedure

2-Methyl-4-[4-[(3S)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]aniline (130 mg, 0.34 mmol) was dissolved in 1,4-dioxane (4 mL). Phenylisocyanate (0.038 mL, 0.34 mmol) was added and the reaction heated at 75° C. for 3 hours. The reaction mixture was evaporated to dryness and the resultant residue triturated with ethyl acetate to give the desired compound as a cream solid (42 mg).

Workup

customThe reaction mixture was evaporated to dryness
customthe resultant residue triturated with ethyl acetate

Sources & evidence

ORD record: ord-09931b81b9204dbca851a303bff37471
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07750003B2

Reaction notes

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