Triphenylphosphine → {1-[(1S,4R)-4-(2,6-Dichloro-purin-9-yl)cyclopent-2-enyl]-1H-pyrazol-4-yl}-methanol

HRID 1929773Notes

Reaction equation

C(OC(=O)O[C@H:6]1[CH2:10][C@@H:9]([N:11]2[CH:19]=[N:18][C:17]3[C:12]2=[N:13][C:14]([Cl:21])=[N:15][C:16]=3[Cl:20])[CH:8]=[CH:7]1)C.[NH:23]1[CH:27]=[C:26]([CH2:28][OH:29])[CH:25]=[N:24]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Cl:21][C:14]1[N:13]=[C:12]2[C:17]([N:18]=[CH:19][N:11]2[C@@H:9]2[CH2:10][C@H:6]([N:23]3[CH:27]=[C:26]([CH2:28][OH:29])[CH:25]=[N:24]3)[CH:7]=[CH:8]2)=[C:16]([Cl:20])[N:15]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture comprising carbonic acid (1S,4R)-4-(2,6-dichloro-purin-9-yl)-cyclopent-2-enyl ester ethyl ester (Intermediate AA2) (1.00 g, 2.92 mmol), (1H-pyrazol-4-yl)-methanol (preparation shown below) (0.34 g, 3.50 mmol) and triphenyl phosphine (0.115 g, 0.44 mmol) in deoxygenated THF (10 mL) under an inert atmosphere of argon is treated with tris(dibenzylideneacetone)dipalladium(0) (0.13 g, 0.15 mmol) and stirred at 50° C. for 1 hour. The solvent is removed in vacuo and the crude product is purified by chromatography on silica eluting with MeOH/DCM (1:25) to yield the title compound.

Workup

customThe solvent is removed in vacuo
customthe crude product is purified by chromatography on silica eluting with MeOH/DCM (1:25)

Sources & evidence

ORD record: ord-7a6062a1c7ae49f09497b2dbedb957b1
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188100B2

Reaction notes

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