(S)-(-)-1-Phenylethyl isocyanate → HCID 10321280, compound

HRID 2216993Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([CH:9]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[CH3:10])=[CH:4][N:3]=1.[CH3:20][C@H:21]([N:28]=[C:29]=[O:30])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([CH:9]([N:11]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[C:29]([NH:28][C@H:21]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH3:20])=[O:30])[CH3:10])=[CH:4][N:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of [1-(2,4-dichloro-pyrimidin-5-yl)-ethyl]-(4-methoxy-phenyl)-amine (378 mg, 1.27 mmol) (from Example 1d supra) and (S)-(−)-α-methylbenzyl isocyanate (205 mg, 1.39 mmol) (Aldrich) in toluene (5 mL) was stirred at 100° C. for 16 hours. After cooling to room temperature the reaction mixture was purified by passing through silica gel and eluting with hexanes-ethyl acetate (1:1) to give 1-[1-(2,4-dichloro-pyrimidin-5-yl)-ethyl]-1-(4-methoxy-phenyl)-3-[1-(S)-phenyl-ethyl]-urea as two separable diastereomers. Less polar diastereomer (thin layer chromatography in hexanes-ethyl acetate, 1:1) (Yield 270 mg, 47.8%) and more polar diastereomer (Yield 284 mg, 50.3%).

Workup

temperatureAfter cooling to room temperature the reaction mixture
customwas purified
washeluting with hexanes-ethyl acetate (1:1)

Sources & evidence

ORD record: ord-ed46c378f96a437c88f617b940771247
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07112676B2

Reaction notes

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