Benzyl Bromide → HCID 19864382, compound

HRID 1199957Notes

Reaction equation

HRID 1199957 reaction equation
[F:1][C:2]([F:24])([F:23])[C:3]1[CH:4]=[C:5]([C:9]2[N:19]3[C:20]4[N:12]([C:13](=[O:22])[NH:14][C:15](=[O:21])[C:16]=4[N:17]=[CH:18]3)[CH2:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1.[H-].[Na+].[CH2:27](Br)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>CN(C)C=O>[C:28]1([CH2:27][N:14]2[C:15](=[O:21])[C:16]3[N:17]=[CH:18][N:19]4[C:9]([C:5]5[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:1])([F:23])[F:24])[CH:4]=5)=[CH:10][CH2:11][N:12]([C:20]=34)[C:13]2=[O:22])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 14677497HCID 14677497, compound

Product 1

HCID 19864382HCID 19864382, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred suspension of 5.0 g of 4-[3-(trifluoromethyl)phenyl]-6H,8H-pyrimido[1,2,3-cd]purine-8,10-(9H)-dione (prepared as described in Example 41) in 50 ml of dry N,N-dimethylformamide at room temperature, under nitrogen, was added 800 mg of sodium hydride (60% dispersion in mineral oil). The mixture was stirred for 2 hours, then 3.1 g of benzyl bromide was added and the mixture was stirred at room temperature for 40 hours. The mixture was evaporated to dryness and treated with water to give a solid. The solid was collected and washed with water and dried. The solid was dissolved in chloroform and passed through a short column of magnesium silicate. The eluate was dried over anhydrous sodium sulfate and filtered. Evaporation of the filtrate gave an orange solid. The solid was triturated with diethyl ether, then filtered. The solid was washed with ether, then hexane and dried to give 4.0 g of the desired product which was recrystallized from ethyl acetate, mp 198°-200° C.

Workup

  1. stirringthe mixture was stirred at room temperature for 40 hours
  2. customThe mixture was evaporated to dryness
  3. additiontreated with water
  4. customto give a solid
  5. customThe solid was collected
  6. washwashed with water
  7. customdried
  8. dissolutionThe solid was dissolved in chloroform
  9. dry with materialThe eluate was dried over anhydrous sodium sulfate
  10. filtrationfiltered
  11. customEvaporation of the filtrate
  12. customgave an orange solid
  13. customThe solid was triturated with diethyl ether
  14. filtrationfiltered
  15. washThe solid was washed with ether
  16. dry with materialhexane and dried

Sources & evidence

ORD record
ord-d1badfb0ba124cae8cbece436b818e0c
Source dataset
uspto-grants-1990_02
Patent number
US04904658

Reaction notes

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