Vinyloxirane → HCID 14408832, compound

HRID 2291855Notes

Reaction equation

HRID 2291855 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][CH:7]=[N:8]2)=[C:4]([Cl:11])[N:3]=1.[CH2:12]=[CH:13][CH:14]1[O:16][CH2:15]1>CN(C)C=O>[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:12]/[CH:13]=[CH:14]\[CH2:15][OH:16])=[C:4]([Cl:11])[N:3]=1

Participants

4

Reactant 2

HCID 13586VinyloxiraneHCID 53603492-Amino-6-chloropurine

Product 1

HCID 14408832HCID 14408832, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

2-Amino-6-chloropurine (3.4 g), butadiene monoepoxide (1.65 g) and tetrakis (triphenylphosphine)palladium (0) (1.0 g) in dry dimethylformamide (75 ml) were stirred under a nitrogen atmosphere and heated at 60° C. for 45 minutes. The solvent was evaporated in vacuum (0.1 mm Mg) and the residue was triturated with hot chloroform (4×50 ml). The combined chloroform solutions were concentrated (25 ml volume) and diluted with ether (100 ml). The gummy precipitate was collected, dried and triturated with hot 1,2-dimethoxyethane (3×50 ml). The combined solutions were evaporated in vacuum (0.1 m Hg) to give a crude mixture (4 g) which was separated on a column of silica gel (500 g) eluted with chloroform+methanol 10+1 (800 ml) followed by chloroform+methanol 8+1. Fractions of about 15 ml were collected and the compound cis-4-(2-Amino-6-chloropurin-9-yl)-2-buten-1-ol was obtained as a minor product (0.2 g) in fractions 74-78. M.p. 160°-165° C.

Workup

  1. customThe solvent was evaporated in vacuum (0.1 mm Mg)
  2. customthe residue was triturated with hot chloroform (4×50 ml)
  3. concentrationThe combined chloroform solutions were concentrated (25 ml volume)
  4. additiondiluted with ether (100 ml)
  5. customThe gummy precipitate was collected
  6. customdried
  7. customtriturated with hot 1,2-dimethoxyethane (3×50 ml)
  8. customThe combined solutions were evaporated in vacuum (0.1 m Hg)
  9. customto give a crude mixture (4 g) which
  10. customwas separated on a column of silica gel (500 g)
  11. washeluted with chloroform+methanol 10+1 (800 ml)
  12. customFractions of about 15 ml were collected

Sources & evidence

ORD record
ord-ad0fcae4cdbd4f5c9d09e1095de8d446
Source dataset
uspto-grants-1989_01
Patent number
US04798833

Reaction notes

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