Methyl iodide → HCID 19864371, compound

HRID 1199955Notes

Reaction equation

HRID 1199955 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+].[CH3:27]I>CN(C)C=O>[CH3:27][N:14]1[C:15](=[O:21])[C:16]2[N:17]=[CH:18][N:19]3[C:9]([C:5]4[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:1])([F:23])[F:24])[CH:4]=4)=[CH:10][CH2:11][N:12]([C:20]=23)[C:13]1=[O:22]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 14677497HCID 14677497, compound

Product 1

HCID 19864371HCID 19864371, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred suspension of 2.0 g of 4-[3-(trifluoromethyl)phenyl]-6H,8H-pyrimido[1,2,3-cd]purine-8,10-(9H)-dione (Example 41) in 20 ml of dry N,N-dimethylformamide was added 310 mg of sodium hydride (60% dispersion in mineral oil). The mixture was stirred at room temperature for 3 hours. To this mixture was added 2.0 ml of methyl iodide with continued stirring for 20 hours. The mixture was concentrated and the residue was treated with water to give a precipitate. The precipitate was collected by filtration, washed with water and dried to give 1.5 g of the desired product which was recrystallized from isopropyl alcohol/acetonitrile, as a white solid, mp 287°-290° C.

Workup

  1. stirringwith continued stirring for 20 hours
  2. concentrationThe mixture was concentrated
  3. additionthe residue was treated with water
  4. customto give a precipitate
  5. filtrationThe precipitate was collected by filtration
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-51cb4faae78644fbabe3f2878c7abf92
Source dataset
uspto-grants-1990_02
Patent number
US04904658

Reaction notes

Loading…