Sodium hydride → HCID 19864378, compound

HRID 1199956Notes

Reaction equation

HRID 1199956 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+].[N+:27]([C:30]1[CH:37]=[CH:36][C:33]([CH2:34]Br)=[CH:32][CH:31]=1)([O-:29])=[O:28]>CN(C)C=O>[N+:27]([C:30]1[CH:37]=[CH:36][C:33]([CH2:34][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:32][CH:31]=1)([O-:29])=[O:28]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 660114-Nitrobenzyl bromideHCID 14677497HCID 14677497, compound

Product 1

HCID 19864378HCID 19864378, compoundYield 61.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

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 3.3 g of p-nitrobenzyl bromide in 10 ml of N,N-dimethylformamide was added and the mixture was stirred at room temperature for 40 hours. The mixture was evaporated to dryness, then was treated with water. The solid formed was collected by filtration, washed with water and dried in vacuo. The solid was stirred with 200 ml of dichloromethane and filtered. The filtrate was passed through a short column of magnesium silicate and the eluate was evaporated in vacuo to give 4.34 g of the product of the example which was recrystallized from isopropyl alcohol/acetonitrile as a white solid, mp 230°-232° C.

Workup

  1. stirringthe mixture was stirred at room temperature for 40 hours
  2. customThe mixture was evaporated to dryness
  3. additionwas treated with water
  4. customThe solid formed
  5. filtrationwas collected by filtration
  6. washwashed with water
  7. customdried in vacuo
  8. stirringThe solid was stirred with 200 ml of dichloromethane
  9. filtrationfiltered
  10. customthe eluate was evaporated in vacuo

Sources & evidence

ORD record
ord-c745d547213b4580b74d4c45640988d7
Source dataset
uspto-grants-1990_02
Patent number
US04904658

Reaction notes

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