1,1'-Thiocarbonyldiimidazole → (3aR,4S,6R,6aS)-4-({[tert-Butyl(dimethyl)silyl]oxy}methyl)-6-{4-[(1S)-2,3-dihydro-1H-inden-1-ylamino]-7H-pyrrolo[2,3-d]pyrimidin-7-yl}tetrahydro-3aH-cyclopenta[d][1,3]dioxole-2-thione

HRID 222171Notes

Reaction equation

[Si:1]([O:8][CH2:9][C@@H:10]1[CH2:14][C@@H:13]([N:15]2[C:19]3[N:20]=[CH:21][N:22]=[C:23]([NH:24][C@@H:25]4[C:33]5[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=5)[CH2:27][CH2:26]4)[C:18]=3[CH:17]=[CH:16]2)[C@H:12]([OH:34])[C@@H:11]1[OH:35])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C:36](N1C=CN=C1)(N1C=CN=C1)=[S:37]>CN(C=O)C>[Si:1]([O:8][CH2:9][C@H:10]1[C@@H:11]2[C@@H:12]([O:34][C:36](=[S:37])[O:35]2)[C@H:13]([N:15]2[C:19]3[N:20]=[CH:21][N:22]=[C:23]([NH:24][C@@H:25]4[C:33]5[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=5)[CH2:27][CH2:26]4)[C:18]=3[CH:17]=[CH:16]2)[CH2:14]1)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of (1S,2R,3S,5R)-3-({[tert-butyl(dimethyl)silyl]oxy}methyl)-5-{4-[(1S)-2,3-dihydro-1H-inden-1-ylamino]-7H-pyrrolo[2,3-d]pyrimidin-7-yl}cyclopentane-1,2-diol (179 mg, 0.362 mmol) in DMF (2.00 mL) under an atmosphere of nitrogen was added 1,1′-thiocarbonyldiimidazole (72.3 mg, 0.406 mmol) and the solution was heated to 80° C. for 3 h. The solvent was removed and the residue was purified by silica gel chromatography eluting with a gradient of 0 to 50% EtOAc in hexanes to afford the title compound (158 mg, 81%). LC/MS: Rt=2.24 min, ES+ 538 (FA standard).

Workup

customThe solvent was removed
customthe residue was purified by silica gel chromatography
washeluting with a gradient of 0 to 50% EtOAc in hexanes

Sources & evidence

ORD record: ord-e41d2c44ca134c368158fe312f2c2c3b
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08207177B2

Reaction notes

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