Sodium methanolate methanol → 5-methyl-3H-pyrrolo[2,3-d]pyrimidin-4(7H)-one

HRID 1291235Notes

Reaction equation

HRID 1291235 reaction equation
S[C:2]1[NH:3][C:4](=[O:12])[C:5]2[C:10]([CH3:11])=[CH:9][NH:8][C:6]=2[N:7]=1.C[O-].[Na+].CO>CO.[Ni]>[CH3:11][C:10]1[C:5]2[C:4](=[O:12])[NH:3][CH:2]=[N:7][C:6]=2[NH:8][CH:9]=1

Participants

5

Reactant 2

HCID 23694274Sodium methanolate methanolHCID 178430835HCID 178430835, compound

Product 1

HCID 1357418185-methyl-3H-pyrrolo[2,3-d]pyrimidin-4(7H)-oneYield 65.3%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

In methanol (714 ml) was suspended 2-mercapto-5-methyl-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 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) δ: 6.44(1H,d,J=3.OHz), 7.03(1H,d,J=3.0 Hz), 7.83(1H,s), 11.80(1H,brs).

Workup

  1. filtrationThe catalyst was then filtered off
  2. distillationThe solvent was 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-5e9661b82e514bbcbd754ee8b4727446
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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