N,N-Diethylaniline → HCID 57972828, compound

HRID 661470Notes

Reaction equation

HRID 661470 reaction equation
P(Cl)(Cl)(Cl)=O.[ClH:6].[N:7]1([C:13]2[CH:14]=[N:15][C:16](O)=[N:17][CH:18]=2)[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1.CCN(C1C=CC=CC=1)CC.C(=O)([O-])O.[Na+]>C(#N)C.C(Cl)(Cl)Cl>[Cl:6][C:16]1[N:15]=[CH:14][C:13]([N:7]2[CH2:12][CH2:11][O:10][CH2:9][CH2:8]2)=[CH:18][N:17]=1

Participants

7

Reactant 4

HCID 7061N,N-DiethylanilineHCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 178479650HCID 178479650, compound

Product 1

HCID 57972828HCID 57972828, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6342AcetonitrileSolvent

Procedure

Phosphoryl chloride (16 ml) was added to a solution of 5-morpholin-4-yl-pyrimidin-2-ol hydrochloride (7.49 g) and diethylaniline (11 ml) in acetonitrile (150 ml) over 10 minutes and the mixture was heated to reflux for 7.5 hours. The reaction mixture was cooled to room temperature, and added to a mixture of a saturated sodium hydrogen carbonate aq. solution and chloroform. The organic layer was washed with a saturated brine, dried over magnesium sulfate and concentrated in vacuo. The resulting residue was purified by column chromatography (silica gel; hexane:ethyl acetate=4:1→1:1) to give the titled compound (4.6 g). MS (m/z): 200/202 [M+H]+.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 7.5 hours
  3. washThe organic layer was washed with a saturated brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified by column chromatography (silica gel; hexane:ethyl acetate=4:1→1:1)

Sources & evidence

ORD record
ord-9d963e1112044d2caafb1438c4d54127
Source dataset
uspto-grants-2011_12
Patent number
US08084611B2

Reaction notes

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