1-Bromo-2-Chloroethane → HCID 14838046, compound

HRID 1165779Notes

Reaction equation

HRID 1165779 reaction equation
[NH2:1][C:2]1[C:10]2[C:9](=[O:11])[N:8]([CH2:12][CH2:13][CH3:14])[C:7](=[O:15])[N:6]([CH2:16][CH2:17][CH2:18][CH3:19])[C:5]=2[NH:4][N:3]=1.Br[CH2:21][CH2:22][Cl:23].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[NH2:1][C:2]1[N:3]([CH2:21][CH2:22][Cl:23])[N:4]=[C:5]2[C:10]=1[C:9](=[O:11])[N:8]([CH2:12][CH2:13][CH3:14])[C:7](=[O:15])[N:6]2[CH2:16][CH2:17][CH2:18][CH3:19]

Participants

5

Reactant 3

HCID 78491-Bromo-2-ChloroethaneHCID 11430Potassium CarbonateHCID 178448716HCID 178448716, compound

Product 1

HCID 14838046HCID 14838046, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-amino-7-butyl-5-propylpyrazolo[3,4-d]pyrimidine-4,6(5H, 7H)-dione(8 g), 1-bromo-2-chloroethane(3.7 ml) and potassium carbonate(6.2 g) in DMF(100 ml) was stirred at 50°-60° C. for 12 hr. The reaction mixture was concentrated to dryness, and the concentrate was extracted with chloroform/water. The chloroform layer was washed with water, dried and concentrated to obtain a brown syrup, which was purified by flash chromatography(silica gel 100 g, chloroform). The purified syrupy product was crystallized from isopropylether to obtain colorless needles(21.5 g,66%), m.p. 118°-121° C.

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. extractionthe concentrate was extracted with chloroform/water
  3. washThe chloroform layer was washed with water
  4. customdried
  5. concentrationconcentrated
  6. customto obtain a brown syrup, which
  7. customwas purified by flash chromatography(silica gel 100 g, chloroform)
  8. customThe purified syrupy product was crystallized from isopropylether

Sources & evidence

ORD record
ord-52bb43caa2de4e209c9fa5f1a3361343
Source dataset
uspto-grants-1990_03
Patent number
US04912104

Reaction notes

Loading…