Ammonia → HCID 13377365, compound

HRID 1632991Notes

Reaction equation

HRID 1632991 reaction equation
N.Cl[C:3]1[N:8]2[C:9]([CH2:12][CH2:13][CH3:14])=[N:10][CH:11]=[C:7]2[CH:6]=[C:5]([Cl:15])[N:4]=1.NC1N2C(CCC)=NC=C2C=C(Cl)N=1.[CH4:30].[OH2:31]>C1CCCCC=1.CO>[Cl:15][C:5]1[N:4]=[C:3]([O:31][CH3:30])[N:8]2[C:9]([CH2:12][CH2:13][CH3:14])=[N:10][CH:11]=[C:7]2[CH:6]=1

Participants

8

Reactant 5

HCID 222AmmoniaHCID 297MethaneHCID 962WaterHCID 13377346HCID 13377346, compound2×HCID 217939465,7-Dichloro-3-propylimidazo[1,5-c]pyrimidine

Product 1

HCID 13377365HCID 13377365, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8079CyclohexeneSolvent

Procedure

To 25 ml of methanol saturated with ammonia gas was added with stirring 1.00 g (4.35 mmole) of 5,7-dichloro-3-(n-propyl)imidazo[1,5-c]pyrimidine (from Example 36). Stirring was continued at 20° C. for 1.5 hours, at which time the mixture was poured into 50 ml of water and extracted with four 35 ml portions of chloroform. The combined extracts were washed twice with 50 ml portions of water, once with 35 ml of saturated aqueous sodium chloride solution and dried over magnesium sulfate. Concentration provided a residue which was triturated with diethyl ether to provide a yellow solid which was mostly 5-amino-7-chloro-3-(n-propyl)imidazo[1,5-c]pyrimidine. The ether solution was evaporated to provide a yellow solid. The solid was dissolved in cyclohexene, treated with decolorizing charcoal and cooled. The small amount of precipitate formed was 5-amino-7-chloro-3-(n-propyl)-imidazo[1,5-c]pyrimidine. Evaporation of the cyclohexane gave yellow solid 7-chloro-5-methoxy-3-(n-propyl)imidazo[1,5-c]pyrimidine, m.p. 76°- 77° C. Analysis: Calculated for C10H12ClN3O: %C, 53.2; %H, 5.4; %N, 18.6; Found; %C, 52.9; %H, 5.4; %N, 18.1 .

Workup

  1. extractionextracted with four 35 ml portions of chloroform
  2. washThe combined extracts were washed twice with 50 ml portions of water, once with 35 ml of saturated aqueous sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. concentrationConcentration
  5. customprovided a residue which
  6. customwas triturated with diethyl ether
  7. customto provide a yellow solid which
  8. customThe ether solution was evaporated
  9. customto provide a yellow solid
  10. temperaturecooled
  11. customThe small amount of precipitate formed
  12. customEvaporation of the cyclohexane

Sources & evidence

ORD record
ord-c3bbb8e73e3c43d1b2e1926611069fd6
Source dataset
uspto-grants-1984_10
Patent number
US04478835

Reaction notes

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