Acetonitrile → HCID 24810832, compound
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)C.[CH3:39][O:40][C:41]1[CH:50]=[C:49]2[C:44]([CH2:45][CH2:46][NH:47][CH:48]2[CH3:51])=[CH:43][C:42]=1[OH:52]>>[Br:1][C:2]1[CH:3]=[N:4][C:5]2[N:6]([N:8]=[C:9]([C:11]([N:47]3[CH2:46][CH2:45][C:44]4[C:49](=[CH:50][C:41]([O:40][CH3:39])=[C:42]([OH:52])[CH:43]=4)[CH:48]3[CH3:51])=[O:13])[CH:10]=2)[CH:7]=1Participants
5
Conditions
- Temperature
- 50 °C
Procedure
To a solution of 6-bromo-pyrazolo[1,5-a]pyrimidine-2-carboxylic acid (1.4 g, 5.8 mmol, 1.0 equiv) and TBTU (2.0 g, 6.2 mmol, 1.1 equiv) in dry acetonitrile (30 mL) triethylamine (2 mL, 14.5 mmol, 2.5 equiv) is added. 7-Methoxy-1-methyl-1,2,3,4-tetrahydro-isoquinolin-6-ol (1.4 g, 7.25 mmol, 1.25 equiv) is then added. The reaction mixture is stirred at 50° C. for 2 h, then at room temperature for 8 h, and concentrated. The residue is extracted with dichloromethane. The extract is washed with water (20 ml), dried over sodium disulfate, and concentrated. The residue is purified by column chromatography on silica gel (eluent: hexane/ethyl acetate—1/1, Rf 0.3) to provide 0.511 g of the title compound as an oil.
Workup
- waitat room temperature for 8 h
- concentrationconcentrated
- extractionThe residue is extracted with dichloromethane
- washThe extract is washed with water (20 ml)
- dry with materialdried over sodium disulfate
- concentrationconcentrated
- customThe residue is purified by column chromatography on silica gel (eluent: hexane/ethyl acetate—1/1, Rf 0.3)
Sources & evidence
- ORD record
- ord-ca3a6728c09d4fdda9f7fdc37a4b36b9
- Source dataset
- uspto-grants-2011_07
- Patent number
- US07985753B2
Reaction notes
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