Ethanol → HCID 11949763, compound

HRID 2243674Notes

Reaction equation

HRID 2243674 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:5]=1[N:11]1[C:16]2[N:17]=[C:18](S(C)(=O)=O)[N:19]=[C:20]([C:21]3[CH:22]=[C:23]([NH:28][C:29](=[O:38])[C:30]4[CH:35]=[CH:34][C:33]([CH3:36])=[C:32]([F:37])[CH:31]=4)[CH:24]=[CH:25][C:26]=3[CH3:27])[C:15]=2[CH2:14][NH:13][C:12]1=[O:43].[CH2:44]([OH:46])[CH3:45]>CCOC(C)=O>[F:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:5]=1[N:11]1[C:16]2[N:17]=[C:18]([O:46][CH2:44][CH3:45])[N:19]=[C:20]([C:21]3[CH:22]=[C:23]([NH:28][C:29](=[O:38])[C:30]4[CH:35]=[CH:34][C:33]([CH3:36])=[C:32]([F:37])[CH:31]=4)[CH:24]=[CH:25][C:26]=3[CH3:27])[C:15]=2[CH2:14][NH:13][C:12]1=[O:43]

Participants

5

Reactant 3

HCID 702Ethanol2×HCID 24758Sodium hydrideHCID 11950100HCID 11950100, compound

Product 1

HCID 11949763HCID 11949763, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

Dry ethanol (2 mL) was treated with NaH (0.0056 mg, 0.140 mmol, 60% in mineral oil) under argon and stirred for 10 min. The compound N-{3-[8-(2,6-difluorophenyl)-2-(methylsulfonyl)-7-oxo-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4-yl]-4-methylphenyl}-3-fluoro-4-methylbenzamide (0.064 g, 0.110 mmol) was added in ethanol (2 mL). The reaction was stirred under argon for 1 h and then warmed to 70° C. for 2 h. The reaction mixture was diluted with EtOAc and the organics washed with water, brine (twice), dried over Na2SO4, filtered and evaporated. The crude residue was purified by flash chromatography on silica gel, eluting with a CH2Cl2—10% EtOAc/CH2Cl2 gradient to afford the title compound as a white solid. mp 257.3-262.5° C.; LC-MS m/z 548 (M+H)+, 2.37 min (ret. time).

Workup

  1. stirringThe reaction was stirred under argon for 1 h
  2. washthe organics washed with water, brine (twice),
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude residue was purified by flash chromatography on silica gel
  7. washeluting with a CH2Cl2—10% EtOAc/CH2Cl2 gradient

Sources & evidence

ORD record
ord-b66418fe27294ff89dcc369599545696
Source dataset
uspto-grants-2010_03
Patent number
US07674789B2

Reaction notes

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