Ethyl cyanoacetate → 6-Amino-2-isopropylpyrimidin-4-ol

HRID 1288284Notes

Reaction equation

HRID 1288284 reaction equation
[Na].[C:2]([CH2:4][C:5](OCC)=[O:6])#[N:3].S(O)(O)(=O)=O.[C:15]([NH2:20])(=[NH:19])[CH:16]([CH3:18])[CH3:17]>C(O)C>[NH2:3][C:2]1[N:19]=[C:15]([CH:16]([CH3:18])[CH3:17])[NH:20][C:5](=[O:6])[CH:4]=1

Participants

5

Reactant 3

HCID 7764Ethyl cyanoacetateHCID 5360545SodiumHCID 86734093Isobutyramidine sulphate

Product 1

HCID 1355966346-Amino-2-isopropylpyrimidin-4-ol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of sodium (1.15 g.) in dry ethanol (20 ml.) was added ethyl cyanoacetate (1.8 ml.) followed after 15 minutes by isobutyramidine sulphate (2.25 g.). The mixture was refluxed for 20 hours, evaporated to dryness, the residue triturated with water (30 ml.) and the pH adjusted to 6 by the addition of hydrochloric acid. After cooling to 0° C, 4-amino-2-isopropylpyrimid-6-one (1.7 g.), m.p. 248°-250° C, was filtered off and recrystallised from ethanol to give 4-amino-2-isopropylpyrimid-6-one (0.95 g.), m.p. 254° C.

Workup

  1. temperatureThe mixture was refluxed for 20 hours
  2. customevaporated to dryness
  3. customthe residue triturated with water (30 ml.)
  4. additionthe pH adjusted to 6 by the addition of hydrochloric acid
  5. filtration4-amino-2-isopropylpyrimid-6-one (1.7 g.), m.p. 248°-250° C, was filtered off
  6. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-dd17df74aff640109d96d6f23b2b97c4
Source dataset
uspto-grants-1976_10
Patent number
US03987160

Reaction notes

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