Sodium hydride → HCID 68160028, compound

HRID 1468792Notes

Reaction equation

HRID 1468792 reaction equation
[H-].[Na+].[S:3]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:12][CH2:11][C@H:10]([CH2:13][OH:14])[CH2:9]2)=[CH:4]1.Cl[C:16]1[N:21]([CH3:22])[C:20](=[O:23])[CH:19]=[C:18]([C:24]2[CH:29]=[CH:28][N:27]=[CH:26][C:25]=2[F:30])[N:17]=1>CN(C)C=O>[F:30][C:25]1[CH:26]=[N:27][CH:28]=[CH:29][C:24]=1[C:18]1[N:17]=[C:16]([O:14][CH2:13][C@H:10]2[CH2:11][CH2:12][N:8]([C:5]3[CH:6]=[CH:7][S:3][CH:4]=3)[CH2:9]2)[N:21]([CH3:22])[C:20](=[O:23])[CH:19]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 595768122-Chloro-3-methyl-6-(3-fluoropyridin-4-yl)-3H-pyrimidin-4-oneHCID 68160022HCID 68160022, compound

Product 1

HCID 68160028HCID 68160028, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a slurry of sodium hydride (60 wt % in mineral oil, 0.04 g, 1.0 mmol) in N,N-dimethylformamide (2 ml) under nitrogen atmosphere was added (S)-[1-(thiophen-3-yl)pyrrolidin-3-yl]methanol (0.13 g, 0.70 mmol) in N,N-dimethylformamide (1 ml) at room temperature. The resulting mixture was stirred for 15 minutes. To the mixture was added 2-chloro-6-(3-fluoro-pyridin-4-yl)-3-methyl-3H-pyrimidin-4-one (0.14 g, 0.60 mmol) at room temperature. After the mixture was stirred for 3 hours, the reaction was quenched with water and partitioned between water and ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography (eluent; hexane/ethyl acetate=90/10 to 0/100) to afford 6-(3-fluoro-pyridin-4-yl)-3-methyl-2-[(3S)-1-thiophen-3-yl-pyrrolidin-3-ylmethoxy]-3H-pyrimidin-4-one (0.045 g, 0.12 mmol, 19%) as a yellow solid.

Workup

  1. stirringAfter the mixture was stirred for 3 hours
  2. customthe reaction was quenched with water
  3. custompartitioned between water and ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography (eluent; hexane/ethyl acetate=90/10 to 0/100)

Sources & evidence

ORD record
ord-a959751f68f9427fbaf94d9236b3cb63
Source dataset
uspto-grants-2015_04
Patent number
US09006232B2

Reaction notes

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