Guanidine, monoacetate → HCID 14011760, compound

HRID 986215Notes

Reaction equation

HRID 986215 reaction equation
[C:1]([O:4][CH:5]([C:9](=O)[CH:10]([CH3:12])[CH3:11])[C:6](=O)[CH3:7])(=[O:3])[CH3:2].C(O)(=O)C.[NH2:18][C:19]([NH2:21])=[NH:20]>CN(C)C=O>[C:1]([O:4][C:5]1[C:9]([CH:10]([CH3:12])[CH3:11])=[N:18][C:19]([NH2:21])=[N:20][C:6]=1[CH3:7])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 2724684Guanidine, monoacetateHCID 20158301HCID 20158301, compound

Product 1

HCID 14011760HCID 14011760, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 3-acetoxy-5-methyl-2,4-hexanedione (5 g, 27 mmol) and guanidine acetate (6.4 g, 54 mmol) in 100 ml dimethylformamide (DMF) was heated at 100° C. for 3 hours. After cooling, the concentrated reaction was filtered through a pad of silica gel using an eluent consisting of equal volume parts of hexane and ethylacetate. The filtrate was concentrated and the residue was treated with excess acetic anhydride in the presence of triethylamine. The reaction mixture was concentrated and the residue was crystallized from boiling hexane to yield 1.7 g (31%) 5-acetoxy-2-amino4-isopropyl-6-methylpyrimidine, m.p. 141°-142° C.

Workup

  1. temperatureAfter cooling
  2. customthe concentrated reaction
  3. filtrationwas filtered through a pad of silica gel using an eluent
  4. concentrationThe filtrate was concentrated
  5. additionthe residue was treated with excess acetic anhydride in the presence of triethylamine
  6. concentrationThe reaction mixture was concentrated
  7. customthe residue was crystallized

Sources & evidence

ORD record
ord-02c8697aae27430dae147ac67897996b
Source dataset
uspto-grants-1987_12
Patent number
US04711888

Reaction notes

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