Triethylamine → 6-Bromo-2-[(4-methyl-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)carbonyl]pyrazolo[1,5-a]pyrimidine
Reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]2[N:6]([N:8]=[C:9]([C:11]([OH:13])=O)[CH:10]=2)[CH:7]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(CC)CC)C.[CH3:43][CH:44]1[C:49]2[CH:50]=[CH:51][S:52][C:48]=2[CH2:47][CH2:46][NH:45]1>C(#N)C.O>[Br:1][C:2]1[CH:3]=[N:4][C:5]2[N:6]([N:8]=[C:9]([C:11]([N:45]3[CH2:46][CH2:47][C:48]4[S:52][CH:51]=[CH:50][C:49]=4[CH:44]3[CH3:43])=[O:13])[CH:10]=2)[CH:7]=1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 50 °C
Procedure
To a solution of 6-bromo-pyrazolo[1,5-a]pyrimidine-2-carboxylic acid (0.7 g, 2.9 mmol, 1.0 equiv) and TBTU (1.0 g, 3.1 mmol, 1.1 equiv) in dry acetonitrile (20 mL), triethylamine (1 mL, 7.25 mmol, 2.5 equiv) and 4-methyl-4,5,6,7-tetrahydro-thieno[3,2-c]pyridine (0.45 g, 2.9 mmol, 1 equiv) are added. The reaction mixture is stirred at 50° C. for 2 h and then at room temperature for 8 h. The reaction mixture is diluted with water (10 ml). The precipitate is filtered, washed sequentially with 50% aqueous ethanol, water, 5% aqueous ammonia, and diethyl ether, and then dried to provide 0.524 g of the title compound.
Workup
- waitat room temperature for 8 h
- filtrationThe precipitate is filtered
- washwashed sequentially with 50% aqueous ethanol, water, 5% aqueous ammonia, and diethyl ether
- customdried
Sources & evidence
- ORD record
- ord-d89a9695ed80473694606d7733426cc9
- Source dataset
- uspto-grants-2011_05
- Patent number
- US07947689B2
Reaction notes
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