1-Bromo-2-Chloroethane → HCID 14986848, compound

HRID 1086831Notes

Reaction equation

HRID 1086831 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][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:5]=2[NH:4][N:3]=1.Br[CH2:24][CH2:25][Cl:26].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[NH2:1][C:2]1[N:3]([CH2:24][CH2:25][Cl:26])[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][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 78491-Bromo-2-ChloroethaneHCID 11430Potassium CarbonateHCID 178456480HCID 178456480, compound

Product 1

HCID 14986848HCID 14986848, compoundYield 60.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-amino-7-benzyl-5-propylpyrazolo[3,4 -d]pyrimidine-4,6(5H,7H)-dione (11 g), 1-bromo-2-chloroethane (8.0 g) and potassium carbonate (7.0 g) was stirred in DMF (120 ml) at 50°-60° C. for 12 hours. The reaction mixture was concentrated to dryness, then the concentrate was extracted with chloroform/water. The chloroform layer was washed with water, dried and concentrated. The resultant brown syrup was purified by flash chromatography (silica gel 100 g, chloroform). The resultant syrup was crystallized from isopropylether to afford colorless needles (8.0 g, 60%), m.p. 126° to 128° 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. customThe resultant brown syrup was purified by flash chromatography (silica gel 100 g, chloroform)
  7. customThe resultant syrup was crystallized from isopropylether

Sources & evidence

ORD record
ord-0fbe763aac9949a39e8aba1c73edb442
Source dataset
uspto-grants-1991_07
Patent number
US05032594

Reaction notes

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