4-(morpholin-4-yl)-5-(1H-pyrazol-4-yl)-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidine → [4-(morpholin-4-yl)-5-(1H-pyrazol-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]methanol

HRID 1750284Notes

Reaction equation

HRID 1750284 reaction equation
[N:1]1([C:7]2[C:8]3[C:15]([C:16]4[CH:17]=[N:18][NH:19][CH:20]=4)=[CH:14][N:13]([CH2:21][O:22]CC[Si](C)(C)C)[C:9]=3[N:10]=[CH:11][N:12]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1>FC(F)(F)C(O)=O>[N:1]1([C:7]2[C:8]3[C:15]([C:16]4[CH:20]=[N:19][NH:18][CH:17]=4)=[CH:14][N:13]([CH2:21][OH:22])[C:9]=3[N:10]=[CH:11][N:12]=2)[CH2:2][CH2:3][O:4][CH2:5][CH2:6]1

Participants

3

Reactant 1

HCID 867069574-(morpholin-4-yl)-5-(1H-pyrazol-4-yl)-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 86706958[4-(morpholin-4-yl)-5-(1H-pyrazol-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]methanolYield 104.1%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

4-(Morpholin-4-yl)-5-(1H-pyrazol-4-yl)-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidine (C20) (0.13 g, 0.32 mmol) was dissolved in trifluoroacetic acid (10 mL) and stirred at room temperature for 2 hours. Removal of solvent in vacuo provided the product (100 mg) as a brown solid; this was used in the next step without further purification. LCMS m/z 301.2 [M+H+].

Workup

  1. customRemoval of solvent in vacuo

Sources & evidence

ORD record
ord-6a8579bbeb534f0bbc1a251718eaf099
Source dataset
uspto-grants-2015_10
Patent number
US09156845B2

Reaction notes

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