Sodium hydride → HCID 22125023, compound

HRID 1858292Notes

Reaction equation

HRID 1858292 reaction equation
[CH2:1]([S:8]([C:11]1[N:16]=[C:15]2[NH:17][C:18](=[O:28])[N:19]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[Br:27])[CH2:20][C:14]2=[CH:13][N:12]=1)(=[O:10])=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:31][O:32][C:33](=[O:42])[C:34]1[CH:39]=[CH:38][CH:37]=[C:36]([CH2:40]Cl)[CH:35]=1>CN(C)C=O>[CH2:1]([S:8]([C:11]1[N:16]=[C:15]2[N:17]([CH2:40][C:36]3[CH:35]=[C:34]([CH:39]=[CH:38][CH:37]=3)[C:33]([O:32][CH3:31])=[O:42])[C:18](=[O:28])[N:19]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[Br:27])[CH2:20][C:14]2=[CH:13][N:12]=1)(=[O:10])=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 3248988Methyl 3-(chloromethyl)benzoateHCID 22124984HCID 22124984, compound

Product 1

HCID 22125023HCID 22125023, compoundYield 56.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A solution of 1 g (2.2 mmol) of 7-benzylsulfonyl-3-(2-bromophenyl)-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one in 20 ml of dimethylformamide was cooled to 0° C. under a nitrogen atmosphere, treated with 112 mg (4.2 mmol) of 60% sodium hydride in mineral oil then stirred for 30 minutes. 440 mg (2.4 mmol) of methyl-3-(chloromethyl)benzoate was added, then the reaction was heated at 90° C. for 3 hours. The solvent was evaporated and the residue partitioned between ethyl acetate (40 ml) and water (40 ml), the ethyl acetate layer was separated, washed with saturated aqueous sodium bicarbonate (40 ml), dried over magnesium sulfate, filtered and evaporated. The crude material was purified by flash chromatography on silica gel, eluting with 1:1 ethyl acetate/hexane. Product containing fractions were combined and evaporated to give 750 mg (56%) of methyl 3-[[7-benzylsulfonyl 3-(2-bromophenyl)-1,2,3,4-tetrahydro-2-oxopyrimido[4,5-d]pyrimid-1-yl]methyl]benzoate as a white solid. [Mass spectrum (ESI) MH+ =607].

Workup

  1. customThe solvent was evaporated
  2. customthe residue partitioned between ethyl acetate (40 ml) and water (40 ml)
  3. customthe ethyl acetate layer was separated
  4. washwashed with saturated aqueous sodium bicarbonate (40 ml)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe crude material was purified by flash chromatography on silica gel
  9. washeluting with 1:1 ethyl acetate/hexane
  10. additionProduct containing fractions
  11. customevaporated

Sources & evidence

ORD record
ord-da51fcc7e045435d96abe7452b3d83d2
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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