Tetrahydrofuran → HCID 67977689, compound

HRID 1468787Notes

Reaction equation

HRID 1468787 reaction equation
[H-].[Na+].C[C:4]1([OH:10])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1.Cl[C:12]1[N:13]([CH3:25])[C:14](=[O:24])[CH:15]=[C:16]([C:18]2[CH:23]=[CH:22][N:21]=[CH:20][N:19]=2)[N:17]=1.O1CCC[CH2:27]1>>[CH3:25][N:13]1[C:14](=[O:24])[CH:15]=[C:16]([C:18]2[CH:23]=[CH:22][N:21]=[CH:20][N:19]=2)[N:17]=[C:12]1[O:10][CH:4]1[CH2:5][CH2:6][CH2:7][CH2:8][CH:9]1[CH3:27]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 115501-MethylcyclohexanolHCID 24758Sodium hydrideHCID 179544602-Chloro-3-methyl-6-(pyrimidin-4-YL)pyrimidin-4-one

Product 1

HCID 67977689HCID 67977689, compoundYield 37%

Conditions

Temperature
40 °C

Procedure

To a solution of sodium hydride (60 wt % in mineral oil, 326 mg, 8.15 mmol) in tetrahydrofuran (14.0 ml) was added 1-methyl cyclohexanol (racemate; cis/trans mixture, 930 mg, 8.15 mmol) at room temperature. The mixture was stirred at 40° C. for one hour. The mixture was cooled to room temperature, and 2-chloro-1-methyl-1H-[4,4′]bipyrimidinyl-6-one (1.51 g, 6.78 mmol) was added to the mixture. The mixture was stirred at 60° C. for 8 hours. The mixture was partitioned between water and ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, and concentrated in vacuo. The residue was purified by silica gel column chromatography (eluent; ethyl acetate) to afford 1-methyl-2-(2-methyl-cyclohexyloxy)-1H-[4,4′]bipyrimidinyl-6-one (cis/trans-mixture) as a colorless solid (752 mg, 2.50 mmol, 37%)

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. stirringThe mixture was stirred at 60° C. for 8 hours
  3. customThe mixture was partitioned between water and ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel column chromatography (eluent; ethyl acetate)

Sources & evidence

ORD record
ord-7f4bb077e86b48d7b25e1c0208d8b21e
Source dataset
uspto-grants-2015_04
Patent number
US09006232B2

Reaction notes

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