Lithium Hydroxide → 4-(3-nitrophenyl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylic acid

HRID 882171Notes

Reaction equation

[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[C:11]3[C:18]([C:19]([O:21]CC)=[O:20])=[CH:17][N:16]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:30])[CH3:29])[C:12]=3[N:13]=[CH:14][N:15]=2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[Li+].[OH-]>CO>[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[C:11]3[C:18]([C:19]([OH:21])=[O:20])=[CH:17][N:16]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:30])[CH3:29])[C:12]=3[N:13]=[CH:14][N:15]=2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of ethyl 4-(3-nitrophenyl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate (2.00 g, 4.52 mmol) in methanol (5 mL) was added LiOH (500 mg, 20.9 mmol). The resulting solution was stirred for 17 hours at 60° C., concentrated in vacuo, and extracted with ethyl acetate (×3). The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo to afford 4-(3-nitrophenyl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylic acid as a yellow solid. LRMS (ESI) calc'd for C19H23N4O5Si [M+H]+: 415, found 415.

Workup

concentrationconcentrated in vacuo
extractionextracted with ethyl acetate (×3)
washThe combined organic layers were washed with brine
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-75b3960d352844f6ac76163527ec833a
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08993756B2

Reaction notes

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