Isopropanol → HCID 11949764, compound

HRID 2243675Notes

Reaction equation

HRID 2243675 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].[CH:44]([OH:47])([CH3:46])[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:47][CH:44]([CH3:46])[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 3776Isopropanol2×HCID 24758Sodium hydrideHCID 11950100HCID 11950100, compound

Product 1

HCID 11949764HCID 11949764, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

Dry iso-propanol (2 mL) was treated with NaH (0.00612 g, 0.153 mmol, 60% in mineral oil) under argon and stirred for 10 min. The product of Example 23d, N-{3-[8-(2,6-difluorophenyl)-2-(methylsulfonyl)-7-oxo-5,6,7,8tetrahydropyrimido[4,5-d]pyrimidin-4-yl]-4-methylphenyl}-3-fluoro-4-methylbenzamide (0.070 g, 0.120 mmol) was added in iso-propanol (2 mL). The reaction was stirred under argon for 1 hour and then warmed to 80° C. for 3 hours. 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 253.5-255.4° C.; LC-MS m/z 562 (M+H)+, 2.44 min (ret. time).

Workup

  1. stirringThe reaction was stirred under argon for 1 hour
  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-38638d07793048a4b74b89aad1e60cd4
Source dataset
uspto-grants-2010_03
Patent number
US07674789B2

Reaction notes

Loading…