Dimethylamine → HCID 11949925, compound

HRID 2243677Notes

Reaction equation

HRID 2243677 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[C:14]2[N:15]=[C:16](S(C)(=O)=O)[N:17]=[C:18]([C:19]3[CH:20]=[C:21]([NH:26][C:27](=[O:36])[C:28]4[CH:33]=[CH:32][C:31]([CH3:34])=[C:30]([F:35])[CH:29]=4)[CH:22]=[CH:23][C:24]=3[CH3:25])[C:13]=2[CH2:12][NH:11][C:10]1=[O:41].[CH3:42][NH:43][CH3:44]>C1COCC1.CCOC(C)=O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[C:14]2[N:15]=[C:16]([N:43]([CH3:44])[CH3:42])[N:17]=[C:18]([C:19]3[CH:20]=[C:21]([NH:26][C:27](=[O:36])[C:28]4[CH:33]=[CH:32][C:31]([CH3:34])=[C:30]([F:35])[CH:29]=4)[CH:22]=[CH:23][C:24]=3[CH3:25])[C:13]=2[CH2:12][NH:11][C:10]1=[O:41]

Participants

5

Reactant 2

HCID 674DimethylamineHCID 11950100HCID 11950100, compound

Product 1

HCID 11949925HCID 11949925, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To 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 (0.075 g, 0.129 mmol) in THF (4 mL) was added a 1.0 M solution of dimethylamine in THF (0.322 mL, 0.322 mmol). The mixture was stirred under argon for 3 days. The completed reaction mixture was diluted with EtOAc and the organic phase washed with water, brine (2×), dried over Na2SO4, filtered and concentrated. The crude residue was purified by flash chromatography on silica gel, eluting with 1% MeOH/CH2Cl2 to afford the title compound as a white solid. mp 257.8-264.3° C.; LC-MS m/z 547 (M+H)+, 2.24 min (ret. time).

Workup

  1. customThe completed reaction mixture
  2. washthe organic phase washed with water, brine (2×)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude residue was purified by flash chromatography on silica gel
  7. washeluting with 1% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-1fc3f93ee6b6453f99ce845a27bbb158
Source dataset
uspto-grants-2010_03
Patent number
US07674789B2

Reaction notes

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