Sodium methanolate methanol → 7-Deazahypoxanthine

HRID 1291234

Reaction equation

HRID 1291234 reaction equation
S[C:2]1[NH:3][C:4](=[O:11])[C:5]2[CH:10]=[CH:9][NH:8][C:6]=2[N:7]=1.C[O-].[Na+].CO>CO.[Ni]>[N:7]1[C:6]2[NH:8][CH:9]=[CH:10][C:5]=2[C:4](=[O:11])[NH:3][CH:2]=1

Participants

5

Reactant 2

HCID 23694274Sodium methanolate methanolHCID 178518762HCID 178518762, compound

Product 1

HCID 1354086897-DeazahypoxanthineYield 66.5%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

In methanol (714 ml) was suspended 2-mercapto-7H-pyrrolo[2,3-d]pyrimidin-4(3H)-one (15.06 g) followed by addition of 28% sodium methoxide/methanol (18.4 ml). While this solution was stirred at 50° C., Raney nickel was added until disappearance of the starting compound had been verified by TLC. The catalyst was then filtered off and the filtrate was neutralized with 1N-HCl (90 ml). The solvent was then distilled off under reduced pressure and the resulting precipitate was collected by filtration, rinsed serially with water, methanol and ether, and dried to provide the title compound (8.1 g). 1H-NMR (DMSO-d6) 8: 6.44(1H,d,J=3.0Hz), 7.03(1H,d,J=3.OHz), 7.83(1H,s), 11.80(1H,brs).

Workup

  1. filtrationThe catalyst was then filtered off
  2. distillationThe solvent was then distilled off under reduced pressure
  3. filtrationthe resulting precipitate was collected by filtration
  4. washrinsed serially with water, methanol and ether
  5. customdried

Sources & evidence

ORD record
ord-518e9f0b1ad34c5aa6dfe261ee7b5f7e
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Linked notes

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