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

HRID 638331

Reaktionsgleichung

Reaktionsgleichung von HRID 638331
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

Komponenten

4

Edukt 2

HCID 10942334Sodium MethoxideHCID 123262194-Methoxybenzamidine Hydrochloride

Produkt 1

HCID 139008192-(4-Methoxyphenyl)pyrimidin-4-amineAusbeute 194,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-396a129928b24d0a948df7e8d00da180
Quelldatensatz
uspto-grants-1985_12
Patentnummer
US04560753

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