Sodium Methoxide → 2-(4-Methoxyphenyl)pyrimidin-4-amine

HRID 638331

Reaction equation

HRID 638331 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]([NH2:10])=[NH:9])=[CH:6][CH:5]=1.C[O-].[Na+]>CO>[CH3:2][O:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]2[N:10]=[C:8]([NH2:9])[CH:7]=[CH:6][N:9]=2)=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 123262194-Methoxybenzamidine Hydrochloride

Product 1

HCID 139008192-(4-Methoxyphenyl)pyrimidin-4-amineYield 194.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The above intermediate 2-(4-methoxyphenyl)-4-pyrimideneamine was prepared as follows: A slurry containing 81 g of 4-methoxybenzamidine hydrochloride, 24 g of sodium methoxide and 200 ml of methanol was stirred for 15 minutes, filtered and the filtrate concentrated in vacuo on a steam bath. To the residue was added β-ethoxyacrylonitrile (same as ethoxymethyleneacetonitrile) and the solution was heated at 100°-115° C. for 2 and 1/2 hours and poured into water. The solid was collected, washed with water, air-dried, and crystallized from ether-n-hexane to yield 85 g of 2-(4-methoxyphenyl)-4-pyrimidinamine, m.p. 102°-104° C.

Workup

  1. customThe above intermediate 2-(4-methoxyphenyl)-4-pyrimideneamine was prepared
  2. filtrationfiltered
  3. concentrationthe filtrate concentrated in vacuo on a steam bath
  4. additionTo the residue was added β-ethoxyacrylonitrile (same as ethoxymethyleneacetonitrile)
  5. temperaturethe solution was heated at 100°-115° C. for 2 and 1/2 hours
  6. additionpoured into water
  7. customThe solid was collected
  8. washwashed with water
  9. customair-dried
  10. customcrystallized from ether-n-hexane

Sources & evidence

ORD record
ord-396a129928b24d0a948df7e8d00da180
Source dataset
uspto-grants-1985_12
Patent number
US04560753

Linked notes

Loading…