Sodium hydride → HCID 59639620, compound

HRID 556604Notes

Reaction equation

HRID 556604 reaction equation
[H-].[Na+].[OH:3][CH2:4][CH:5]([CH2:8][OH:9])[CH2:6][OH:7].[F:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[C:12]=1[N:18]1[C:23]2[N:24]=[C:25](S(C)(=O)=O)[N:26]=[C:27]([C:28]3[CH:33]=[CH:32][C:31]([F:34])=[CH:30][C:29]=3[CH3:35])[C:22]=2[CH:21]=[CH:20][C:19]1=[O:40]>C1COCC1>[F:17][C:13]1[CH:14]=[CH:15][CH:16]=[C:11]([F:10])[C:12]=1[N:18]1[C:23]2[N:24]=[C:25]([O:3][CH2:4][CH:5]([CH2:8][OH:9])[CH2:6][OH:7])[N:26]=[C:27]([C:28]3[CH:33]=[CH:32][C:31]([F:34])=[CH:30][C:29]=3[CH3:35])[C:22]=2[CH:21]=[CH:20][C:19]1=[O:40]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 78432TrimethylolmethaneHCID 596395548-(2,6-difluoro-phenyl)-4-(4-fluoro-2-methyl-phenyl)-2-methanesulfonyl-8H-pyrido[2,3-d]pyrimidin-7-one

Product 1

HCID 59639620HCID 59639620, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

NaH (15 mg, 0.6 mmol) was added to 2-(hydroxymethyl)-1,3-propanediol in THF (5 mL). The mixture was allowed to stir at 23° under Ar for 10 min and was then cooled to −78°. The product of Example 48 (224 mg, 0.5 mmol) in THF (5 mL) was added at −78° and the mixture allowed to warm to 23° and stir for 2 h. The solvents were removed in vacuo, and the residue was partitioned between EtOAc and H2O. The organic phase was washed with H2O, satd aq NaCl, dried over anhyd Na2SO4, filtered and evaporated to give the crude product. Flash chromatography eluted with 70% EtOAc/CH2Cl2 the title compound as a white-amorphous solid. mp 77-81°, LC MS m/z=472 (MH+) Retention time=1.79 min.

Workup

  1. temperaturewas then cooled to −78°
  2. temperatureto warm to 23°
  3. stirringstir for 2 h
  4. customThe solvents were removed in vacuo
  5. customthe residue was partitioned between EtOAc and H2O
  6. washThe organic phase was washed with H2O
  7. dry with materialdried over anhyd Na2SO4
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-9e262a131d6742159d072e20327db0f7
Source dataset
uspto-grants-2011_11
Patent number
US08058282B2

Reaction notes

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