Ethanol → 2,4-Diamino-6-ethoxypyrimidine

HRID 1178217Notes

Reaction equation

HRID 1178217 reaction equation
[Na].Cl[C:3]1[CH:8]=[C:7]([NH2:9])[N:6]=[C:5]([NH2:10])[N:4]=1.[CH2:11]([OH:13])[CH3:12]>>[NH2:10][C:5]1[N:4]=[C:3]([O:13][CH2:11][CH3:12])[CH:8]=[C:7]([NH2:9])[N:6]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 674322,4-Diamino-6-chloropyrimidineHCID 5360545Sodium

Product 1

HCID 2226632,4-Diamino-6-ethoxypyrimidineYield 72%

Conditions

Temperature
160 °C

Procedure

To a solution of sodium (1.05 g) in ethanol (50 ml) was added 4-chloro-2,6-diaminopyrimidine (6 g, 41.4 mmoles). The resulting solution was heated in a reactor for 6 hours at 160° C. The reaction mixture was cooled down and the precipitated sodium chloride was filtered off. The filtrate was concentrated and precipitated from ethanol (two times), affording the pure title compound as a white solid (4.53 g, 72% yield). The spectral data are identical to those described e.g. by W. Pfleiderer et al. in Chem. Ber. (1961) 94, 12.

Workup

  1. temperatureThe reaction mixture was cooled down
  2. filtrationthe precipitated sodium chloride was filtered off
  3. concentrationThe filtrate was concentrated
  4. customprecipitated from ethanol (two times)

Sources & evidence

ORD record
ord-cf21168e04f7416abaf2728d23748656
Source dataset
uspto-grants-2007_10
Patent number
US07276506B2

Reaction notes

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