Carbonic acid-guanidine (1:1) → 4-Cyclopropyl-6-methyl-2-pyrimidinamine

HRID 462346Notes

Reaction equation

HRID 462346 reaction equation
C(=O)(O)O.[NH2:5][C:6]([NH2:8])=[NH:7].[CH:9]1([C:12](=O)[CH2:13][C:14](=O)[CH3:15])[CH2:11][CH2:10]1>O>[NH2:7][C:6]1[N:8]=[C:12]([CH:9]2[CH2:11][CH2:10]2)[CH:13]=[C:14]([CH3:15])[N:5]=1

Participants

4

Reactant 2

HCID 286947Carbonic acid-guanidine (1:1)HCID 110188691-Cyclopropyl-butane-1,3-dione

Product 1

HCID 136726584-Cyclopropyl-6-methyl-2-pyrimidinamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
95 °C

Procedure

15 g of guanidine carbonate are added to a mixture of 10 g of 1-cyclopropyl-butane-1,3-dione and 150 g of water, and stirring is maintained at 95° C. for 5 hours. The mixture is then concentrated by evaporation to a volume of 50 ml, and the cooled aqueous concentrate is extracted three times with 100 ml of ethylene chloride each time. The organic phase is dried over magnesium sulfate and concentrated by evaporation. The residue crystallises to thus yield 5 g of the title compound, m.p. 113°-115° C.

Workup

  1. concentrationThe mixture is then concentrated by evaporation to a volume of 50 ml
  2. concentrationthe cooled aqueous concentrate
  3. extractionis extracted three times with 100 ml of ethylene chloride each time
  4. dry with materialThe organic phase is dried over magnesium sulfate
  5. concentrationconcentrated by evaporation
  6. customThe residue crystallises to thus yield 5 g of the title compound, m.p. 113°-115° C.

Sources & evidence

ORD record
ord-30d619e8a99e4976ab7eadc900b6c30c
Source dataset
uspto-grants-1985_05
Patent number
US04515626

Reaction notes

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