Water → 3-[4-(7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]pentanal
Reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]2[C:7]3[CH:14]=[CH:13][N:12]([CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[C:8]=3[N:9]=[CH:10][N:11]=2)[CH:3]=[N:2]1.C1CCN2C(=NCCC2)CC1.[CH:34](=[O:39])/[CH:35]=[CH:36]/[CH2:37][CH3:38].O>C(#N)C>[CH3:20][Si:19]([CH3:22])([CH3:21])[CH2:18][CH2:17][O:16][CH2:15][N:12]1[C:8]2[N:9]=[CH:10][N:11]=[C:6]([C:4]3[CH:5]=[N:1][N:2]([CH:36]([CH2:37][CH3:38])[CH2:35][CH:34]=[O:39])[CH:3]=3)[C:7]=2[CH:14]=[CH:13]1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 4-(1H-pyrazol-4-yl)-7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]-pyrimidine (100 mg, 0.0003 mol) in ACN (2 mL, 0.04 mol) and DBU (50 mL, 0.0003 mol), the (2E)-pent-2-enal (4.0E1 mg, 0.00048 mol) in 1 ml ACN was added drop wise. The reaction was stirred for 1 h, and then water was added and the resulting mixture extracted with ethyl acetate. The combined organic layers were washed with saturated sodium chloride, dried over magnesium sulfate, filtered and concentrated to give the crude as the hydrated product form. LC/MS (M+H)+: m/z=400.
Workup
- extractionthe resulting mixture extracted with ethyl acetate
- washThe combined organic layers were washed with saturated sodium chloride
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated
- customto give the crude as the hydrated product form
Sources & evidence
- ORD record
- ord-ae37896f378d4ad2b59581330db83e31
- Source dataset
- uspto-grants-2015_01
- Patent number
- US08933086B2
Reaction notes
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