1-Bromopropane → HCID 13339929, compound

HRID 2418682Notes

Reaction equation

HRID 2418682 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[CH:11]=[N:10][CH:9]([CH3:12])[N:5]2[C:6](=[O:8])[N:7]=1.[H-].[Na+].Br[CH2:16][CH2:17][CH3:18]>O1CCOCC1>[Cl:1][C:2]1[N:7]([CH2:16][CH2:17][CH3:18])[C:6](=[O:8])[N:5]2[C:9]([CH3:12])=[N:10][CH:11]=[C:4]2[CH:3]=1

Participants

5

Reactant 3

HCID 78401-BromopropaneHCID 24758Sodium hydrideHCID 70454969HCID 70454969, compound

Product 1

HCID 13339929HCID 13339929, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a mixture of 2.0 g (10.9 mmole) of 7-chloro-3-methylimidazo[1,5-c]pyrimidin-5-one (from Example 4, Part B) in 50 ml of dioxane was added 0.52 g (13 mmole) of 60% sodium hydride in oil. After ten minutes of stirring, 1.6 g (13 mmole) of 3-bromopropane was added and the mixture was stirred for 16 hours at 50° C. The solution was poured into 100 ml of an ice water mixture. The resulting solution was extracted four times with 75 ml portions of chloroform. The extracts were washed twice with water, dried, and evaporated. The residue was dissolved in 80 ml of chloroform, washed with six 100 ml portions of water, dried and evaporated. The residue was recrystallized with treatment with decolorizing charcoal from cyclohexane to provide 7-chloro-3-methyl-6-n-propylimidazo[1,5-c]pyrimidin-5-one, m.p. 125°-126° C. Analysis: Calculated for C10H12ClNO: %C, 53.2 ; %H, 5.4; %N, 18.6; Found: %C, 53.5; %H, 5.3; %N, 18.6.

Workup

  1. stirringthe mixture was stirred for 16 hours at 50° C
  2. extractionThe resulting solution was extracted four times with 75 ml portions of chloroform
  3. washThe extracts were washed twice with water
  4. customdried
  5. customevaporated
  6. dissolutionThe residue was dissolved in 80 ml of chloroform
  7. washwashed with six 100 ml portions of water
  8. customdried
  9. customevaporated
  10. customThe residue was recrystallized with treatment with decolorizing charcoal from cyclohexane

Sources & evidence

ORD record
ord-14af5294041d49db8632775f0a95e610
Source dataset
uspto-grants-1984_09
Patent number
US04473570

Reaction notes

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