Carbonic acid-guanidine (1:1) → Aditeren

HRID 867608Notes

Reaction equation

HRID 867608 reaction equation
C[O-].[Na+].C(=O)(O)O.[NH2:8][C:9]([NH2:11])=[NH:10].[NH2:12][C:13]1[C:29]([O:30][CH3:31])=[CH:28][C:16]([CH2:17][C:18](=[CH:21]N2CCOCC2)[C:19]#[N:20])=[CH:15][C:14]=1[O:32][CH3:33]>CS(C)=O.O>[NH2:10][C:9]1[N:11]=[C:19]([NH2:20])[C:18]([CH2:17][C:16]2[CH:15]=[C:14]([O:32][CH3:33])[C:13]([NH2:12])=[C:29]([O:30][CH3:31])[CH:28]=2)=[CH:21][N:8]=1

Participants

6

Reactant 3

HCID 286947Carbonic acid-guanidine (1:1)HCID 10942334Sodium MethoxideHCID 54194946HCID 54194946, compound

Product 1

HCID 176875Aditeren

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 6.5 g of sodium methylate, 21.6 g of guanidine carbonate and 12.8 g of α-(4-amino-3,5-dimethoxy-benzyl)-β-morpholino - acrylonitrile in 120 ml of absolute dimethyl sulphoxide was stirred at 120° C. for 60 hours. Subsequently, the mixture was diluted with 1.2 liters of water and extracted with two 2 liter portions of ethyl acetate. The ethyl acetatae extract was washed with two 1 liter portions of water, dried over magnesium sulphate and evaporated in vacuo. After recrystallisation of the residue from methanol, there was obtained 2,4-diamino-5-(4-amino-3,5-dimethoxy-benzyl)-pyrimidine of melting point 215°-216° C.

Workup

  1. extractionextracted with two 2 liter portions of ethyl acetate
  2. extractionThe ethyl acetatae extract
  3. washwas washed with two 1 liter portions of water
  4. dry with materialdried over magnesium sulphate
  5. customevaporated in vacuo
  6. customAfter recrystallisation of the residue from methanol

Sources & evidence

ORD record
ord-13eddc10a04c4dbcae697135b84fe457
Source dataset
uspto-grants-1988_10
Patent number
US04775756

Reaction notes

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