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

HRID 2353621Notes

Reaction equation

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

Participants

Conditions

Temperature: 70 °C

Procedure

4-[4-[(3S)-3-Methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]aniline (100 mg, 0.28 mmol) was dissolved in dioxane (4 mL). Ethylisocyanate (0.109 mL, 1.38 mmol) was added and the reaction heated at 70° C. for 4 hours. Reaction was complete and was evaporated to dryness. The resultant oil was purified by chromatography, eluting with 10-50% ethyl acetate in isohexane, to give 3-ethyl-1-[4-[4-[(3S)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]phenyl]urea as a pale yellow oil (113 mg, 94%).

Workup

customReaction
customwas evaporated to dryness
customThe resultant oil was purified by chromatography
washeluting with 10-50% ethyl acetate in isohexane

Sources & evidence

ORD record: ord-d58ef7d8b3cb474b8e75e3b04e04eaca
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07750003B2

Reaction notes

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