Methanol → HCID 178418823, compound

HRID 1168300Notes

Reaction equation

HRID 1168300 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 28) (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) were added and heating was continued for a further 24 hours. The reaction mixture was allowed to cool and the solvent was removed under reduced pressure. The residue was dissolved in tetrahydrofuran (375 ml), 2 M aqueous hydrochloric acid (125 ml) was added and the mixture was stirred at room temperature for 24 hours. The tetrahydrofuran was removed under reduced pressure and the pH of the suspension was adjusted to 7 with saturated aqueous sodium bicarbonate solution. Ethyl acetate (100 ml) was added and the white solid consisting mainly of the desired product was filtered, washed with a little water and 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). Evaporation of the ethyl acetate filtrate provided 2.6 g of the starting material.

Workup

  1. temperatureunder reflux for 24 hours
  2. temperatureheating
  3. temperatureto cool
  4. customthe solvent was removed under reduced pressure
  5. dissolutionThe residue was dissolved in tetrahydrofuran (375 ml)
  6. addition2 M aqueous hydrochloric acid (125 ml) was added
  7. customThe tetrahydrofuran was removed under reduced pressure
  8. additionEthyl acetate (100 ml) was added
  9. filtrationwas filtered
  10. washwashed with a little water and ethyl acetate
  11. customdried
  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-528e7da294da42ba9882d7f433c0dd30
Source dataset
uspto-grants-2003_09
Patent number
US06624158B2

Reaction notes

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