7H-Pyrrolo(2,3-d)pyrimidine, 4-chloro- → 4-Methoxy-7h-pyrrolo[2,3-d]pyrimidine

HRID 854385Notes

Reaction equation

HRID 854385 reaction equation
[CH3:1][O-:2].[Na+].[Na].Cl[C:6]1[C:7]2[CH:14]=[CH:13][NH:12][C:8]=2[N:9]=[CH:10][N:11]=1>CO>[CH3:1][O:2][C:6]1[C:7]2[CH:14]=[CH:13][NH:12][C:8]=2[N:9]=[CH:10][N:11]=1

Participants

5

Reactant 3

HCID 53566827H-Pyrrolo(2,3-d)pyrimidine, 4-chloro-HCID 5360545SodiumHCID 10942334Sodium Methoxide

Product 1

HCID 2487924-Methoxy-7h-pyrrolo[2,3-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of sodium methoxide prepared by adding portion wise the sodium (2 g) in methanol (100 mL) under an inert atmosphere, was added 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (Reference: Gerster, John F.; Hinshaw, Barbara C.; Robins, Roland K.; Townsend, Leroy B. Study of electrophylic substitution in the pyrrolo[2,3-d]pyrimidine ring. J. Heterocycl. Chem. (1969), -(2), 207-13.) (3.5 g). The solution was stirred at 65° C. for 16 hours and then partitioned between ethyl acetate and brine. The organic phase was separated, then dried over magnesium sulfate and then evaporated under reduced pressure. The residue was subjected to flash column chromatography on silica eluting with a mixture of ethyl acetate and cyclohexane (50:50, v/v) to give the title compound (1.2 g) as an amorphous solid. MS: 150 [MH]+. LCMS (Method B) RT=2.39 minutes.

Workup

  1. custompartitioned between ethyl acetate and brine
  2. customThe organic phase was separated
  3. dry with materialdried over magnesium sulfate
  4. customevaporated under reduced pressure
  5. additionThe residue was subjected to flash column chromatography on silica eluting with a mixture of ethyl acetate and cyclohexane (50:50

Sources & evidence

ORD record
ord-05114e39256b4c5b92373cae773de061
Source dataset
uspto-grants-2007_08
Patent number
US07259154B2

Reaction notes

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