Sodium Methoxide → HCID 13068467, compound

HRID 1759134Notes

Reaction equation

HRID 1759134 reaction equation
Cl[C:2]1[C:3]2[CH2:11][CH2:10][O:9][C:4]=2[N:5]=[C:6]([NH2:8])[N:7]=1.[CH3:12][O-:13].[Na+]>CO>[CH3:12][O:13][C:2]1[C:3]2[CH2:11][CH2:10][O:9][C:4]=2[N:5]=[C:6]([NH2:8])[N:7]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 13068466HCID 13068466, compound

Product 1

HCID 13068467HCID 13068467, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 27 g of 4-chloro-5,6-dihydrofuro[2,3-d]pyrimidin-2-amine in 500 ml of anhydrous methanol was added 22 g of sodium methoxide and the mixture was heated to reflux (66°) for 5.5 hours. The solvent was then removed under reduced pressure and the residue triturated with water (500 ml) then filtered and rinsed well with water. The solid was air dried to give 20 g of 5,6-dihydro-4-methoxyfuro[2,3-d]pyrimidin-2-amine, m.p. 172°-177°. Two triplet absorptions at 3.42 and 5.02 ppm and a singlet absorption at 4.21 ppm in the nuclear magnetic resonance spectrum (60 MHz), indicated the title compound.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux (66°) for 5.5 hours
  3. customThe solvent was then removed under reduced pressure
  4. customthe residue triturated with water (500 ml)
  5. filtrationthen filtered
  6. washrinsed well with water
  7. customdried

Sources & evidence

ORD record
ord-bf2f2a1cd3f94aa6a4b6f9382c958f61
Source dataset
uspto-grants-1982_07
Patent number
US04339267

Reaction notes

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