Triphenylphosphine → HCID 69183175, compound

HRID 133027Notes

Reaction equation

[C:1]1([C@H:7]([NH:9][C:10]2[C:11]3[CH:18]=[C:17]([C:19]4[CH:20]=[C:21]([CH2:25]O)[CH:22]=[CH:23][CH:24]=4)[NH:16][C:12]=3[N:13]=[CH:14][N:15]=2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:46]N1C(=O)CCC1=O>ClCCl>[Cl:46][CH2:25][C:21]1[CH:20]=[C:19]([C:17]2[NH:16][C:12]3[N:13]=[CH:14][N:15]=[C:10]([NH:9][C@@H:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[CH3:8])[C:11]=3[CH:18]=2)[CH:24]=[CH:23][CH:22]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of 688 mg (2 mmol) {3-[4-((R)-1-phenyl-ethylamino)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-phenyl}-methanol and 578 mg (2.2 mmol) triphenylphosphine in 60 ml dichloromethane is treated at 0° C. with 293 mg (2.2 mmol) N-chlorosuccinimide. After stirring 1 h at 0° C. all the material has gone into solution. The solvent is evaporated and the title compound purified with flash chromatography using dichloromethane/ethanol 95:5 (the title compound is contaminated with a small amount of triphenylphosphine oxide); Rf (dichloromethane/ethanol 95:5)=0.35; MS-ES+: (M+H)+=363.

Workup

customThe solvent is evaporated
customthe title compound purified with flash chromatography

Sources & evidence

ORD record: ord-9edcfdea7b7942adad156ba32bf4a4bb
Source dataset: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07390805B2

Reaction notes

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