Acetonitrile → 4-(2-Pyrimidinyl)-3-butynol
Reaction equation
Br[C:2]1[N:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[CH2:8]([OH:12])[CH2:9][C:10]#[CH:11].C1(NC2CCCCC2)CCCCC1.C(#N)C>[Cu]I.CCOCC>[N:3]1[CH:4]=[CH:5][CH:6]=[N:7][C:2]=1[C:11]#[C:10][CH2:9][CH2:8][OH:12]Participants
7
Procedure
A mixture of 2-bromopyrimidine (5.0 g), 3-butynol (2.20 g), dicyclohexylamine (6.87 g), copper (I) iodide (50 mg), BTPC (380 mg) and acetonitrile (50 ml) was stirred at room temperature under nitrogen for 16 h. Ether (150 ml) was added, the mixture filtered and the filtrate evaporated in vacuo. Purification of the residue by FCC eluting with ether and ether-methanol (1-3%) followed by System C (5:1) afforded the title compound as a pale yellow solid (4.29 g) m.p. 58°-64°, t.l.c. (System C, 99:1) Rf 0.08
Workup
- filtrationthe mixture filtered
- customthe filtrate evaporated in vacuo
- customPurification of the residue by FCC
- washeluting with ether and ether-methanol (1-3%)
Sources & evidence
- ORD record
- ord-16cb4801153c4a778289d3588af01b79
- Source dataset
- uspto-grants-1992_09
- Patent number
- US05149698
Reaction notes
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