Acetic Acid → 4-Pyrimidinol, 6-methyl-5-propyl-

HRID 916635Notes

Reaction equation

HRID 916635 reaction equation
C[O-].[Na+].[CH:4]([NH2:6])=[NH:5].C[O:8][C:9](=O)[CH:10]([C:14](=O)[CH3:15])[CH2:11][CH2:12][CH3:13].C(O)(=O)C>CO>[CH2:11]([C:10]1[C:9](=[O:8])[NH:5][CH:4]=[N:6][C:14]=1[CH3:15])[CH2:12][CH3:13]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 68047FormamidineHCID 10942334Sodium MethoxideHCID 14360044Methyl 2-acetylpentanoate

Product 1

HCID 1355027734-Pyrimidinol, 6-methyl-5-propyl-

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

NaOMe (1.30 g, 24 mmol) is added to a stirred solution of formamidine (12 mmol) in MeOH (75 ml) at room temperature. The mixture is stirred for 15 minutes. 2-Acetyl-pentanoic acid methyl ester (10 mmol) is added and the mixture is stirred at room temperature overnight. Acetic acid (0.72 g, 12 mmol) is added and the solvent is removed in vacuo. Water (30 ml) is added to the residue and it is extracted with 2-butanone (3×30 ml). The combined extracts are washed with brine (40 ml), dried (Na2SO4) and evaporated, to provide a yellow solid (100), which is used in the next step without further purification.

Workup

  1. stirringthe mixture is stirred at room temperature overnight
  2. customthe solvent is removed in vacuo
  3. additionWater (30 ml) is added to the residue and it
  4. extractionis extracted with 2-butanone (3×30 ml)
  5. washThe combined extracts are washed with brine (40 ml)
  6. dry with materialdried (Na2SO4)
  7. customevaporated

Sources & evidence

ORD record
ord-81e28272e9524300a4369e301ab93afd
Source dataset
uspto-grants-2007_09
Patent number
US07271170B2

Reaction notes

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