Methanol → HCID 178418823, compound

HRID 2184270Notes

Reaction equation

HRID 2184270 reaction equation
[C:1]1([CH:7]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:8][NH:9][C:10]2[N:18]=[C:17]([C:19]#N)[N:16]=[C:15]3[C:11]=2[N:12]=[CH:13][NH:14]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:27][O-:28].[Na+].C[OH:31]>>[C:1]1([CH:7]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:8][NH:9][C:10]2[N:18]=[C:17]([C:19]([O:28][CH3:27])=[O:31])[N:16]=[C:15]3[C:11]=2[N:12]=[CH:13][NH:14]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 887Methanol2×HCID 10942334Sodium Methoxide2×HCID 178419062HCID 178419062, compound

Product 1

HCID 178418823HCID 178418823, compound

Procedure

A solution of 6-[(2,2-diphenylethyl)amino]-9H-purine-2-carbonitrile (Preparation 15) (5.0 g, 14.7 mmol) and sodium methoxide (4.0 g, 74.1 mmol) in methanol (300 ml) was heated under reflux for 24 hours. Further sodium methoxide (2.0 g, 37 mmol) and methanol (100 ml) was then added and heating continued for a further 24 hours. The reaction mixture was cooled and the solvent removed under reduced pressure. The residue was dissolved in tetrahydrofuran (375 ml), 2 M aqueous hydrochloric acid solution (125 ml) added and the mixture stirred at room temperature for 24 hours. The tetrahydrofuran was removed under reduced pressure and the pH of the suspension adjusted to 7 with saturated aqueous sodium bicarbonate solution. Ethyl acetate (100 ml) was then added and the suspended white solid filtered off, washed with a little water then ethyl acetate and dried. Purification by column chromatography on silica gel eluting with a gradient system of dichloromethane:methanol (90:10, by volume) gradually changing to dichloromethane:methanol (75:25, by volume) afforded the title compound as a white solid (1.25 g) (n.b. evaporation of the ethyl acetate filtrate provided 2.6 g of the starting material).

Workup

  1. temperatureunder reflux for 24 hours
  2. temperatureheating
  3. temperatureThe reaction mixture was cooled
  4. customthe solvent removed under reduced pressure
  5. dissolutionThe residue was dissolved in tetrahydrofuran (375 ml)
  6. addition2 M aqueous hydrochloric acid solution (125 ml) added
  7. customThe tetrahydrofuran was removed under reduced pressure
  8. additionEthyl acetate (100 ml) was then added
  9. filtrationthe suspended white solid filtered off
  10. washwashed with a little water
  11. dry with materialethyl acetate and dried
  12. customPurification by column chromatography on silica gel eluting with a gradient system of dichloromethane:methanol (90:10, by volume)

Sources & evidence

ORD record
ord-44539b854ff347999157ecd514b7cad6
Source dataset
uspto-grants-2005_05
Patent number
US06900309B1

Reaction notes

Loading…