Sodium Hydroxide → HCID 86633619, compound

HRID 1855402Notes

Reaction equation

HRID 1855402 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:12]3[N:17]=[C:16]([CH3:18])[N:15]=[C:14](O)[CH:13]=3)[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:22])=O.[OH-].[Na+]>ClCCl>[Cl:22][C:14]1[CH:13]=[C:12]([C:8]2([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)[CH2:11][CH2:10][CH2:9]2)[N:17]=[C:16]([CH3:18])[N:15]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 178433444HCID 178433444, compound

Product 1

HCID 86633619HCID 86633619, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

To 6-[1-(4-chlorophenyl)cyclobutyl]-2-methylpyrimidin-4-ol (1.00 g, 3.65 mmol) was added phosphorous oxychloride (10 mL) and the mixture was refluxed for 1.5 h. After cooling to 20° C., the reaction mixture was poured into ice/water (55 mL). After the addition of dichloromethane, the mixture was neutralized with 32% aqueous sodium hydroxide solution. The layers were separated and the organic layer was washed with 0.1 N sodium hydroxide solution and with water, dried over magnesium sulfate, and evaporated under reduced pressure. The residual material was purified by chromatography on silica gel using dichloromethane/methanol (95:5 v/v) as eluent to afford the title compound (0.91 g, 85%) as an off-white solid. Mp 96-98° C.

Workup

  1. temperaturethe mixture was refluxed for 1.5 h
  2. customThe layers were separated
  3. washthe organic layer was washed with 0.1 N sodium hydroxide solution and with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated under reduced pressure
  6. customThe residual material was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-e4daea1af9d9446b8f4db267aff279c5
Source dataset
uspto-grants-2015_02
Patent number
US08962834B2

Reaction notes

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