Ammonia methanol → (2S,4S)-tert-butyl 4-(4-amino-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2-((tert-butyldiphenylsilyloxy)methyl)pyrrolidine-1-carboxylate

HRID 516174Notes

Reaction equation

CO.[NH3:3].[Si:4]([O:21][CH2:22][C@@H:23]1[CH2:27][C@H:26]([N:28]2[C:32]3[N:33]=[CH:34][N:35]=[C:36](Cl)[C:31]=3[C:30]([I:38])=[CH:29]2)[CH2:25][N:24]1[C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])([C:17]([CH3:20])([CH3:19])[CH3:18])([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>C1COCC1>[NH2:3][C:36]1[C:31]2[C:30]([I:38])=[CH:29][N:28]([C@@H:26]3[CH2:25][N:24]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[C@H:23]([CH2:22][O:21][Si:4]([C:17]([CH3:20])([CH3:19])[CH3:18])([C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=4)[C:5]4[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=4)[CH2:27]3)[C:32]=2[N:33]=[CH:34][N:35]=1

Participants

Conditions

Temperature: 120 °C

Procedure

THF (10 ml) and an 8N ammonia methanol solution (5 ml) were added to the (2S,4S)-tert-butyl 2-((tert-butyldiphenylsilyloxy)methyl)-4-(4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)pyrrolidine-1-carboxylate (400 mg) obtained in Step 1. The mixture was stirred at 120° C. for 2 hours under microwave irradiation, and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (developing solvent: chloroform/ethanol) to obtain the title compound as a light-yellow solid (293 mg). Physical properties: m/z [M+H]+ 698.5

Workup

distillationthe solvent was distilled off under reduced pressure
customThe resulting residue was purified by silica gel column chromatography (developing solvent: chloroform/ethanol)

Sources & evidence

ORD record: ord-b7e2e33790b84c22ba57a8cf1f9d2330
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09108973B2

Reaction notes

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