Acetonitrile → HCID 19876771, compound

HRID 1886008Notes

Reaction equation

HRID 1886008 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

Reactant 4

HCID 6342AcetonitrileHCID 7582DicyclohexylamineHCID 135663-Butyn-1-OLHCID 783452-Bromopyrimidine

Product 1

HCID 19876771HCID 19876771, compoundYield 92.2%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 3283Diethyl EtherSolvent

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

  1. filtrationthe mixture filtered
  2. customthe filtrate evaporated in vacuo
  3. customPurification of the residue by FCC
  4. 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

Loading…