Acetonitrile → (1R)-2-{[2-Cyclopropyl-6-(3,4-dichlorophenyl)pyrimidin-4-yl]amino}-1-phenylethanol

HRID 1908248Notes

Reaction equation

HRID 1908248 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([Cl:15])[CH:9]=2)[N:5]=[C:4]([CH:16]2[CH2:18][CH2:17]2)[N:3]=1.C1(C2N=C(O)C=C([C:29]3[CH:34]=[CH:33][C:32](Cl)=[C:31](Cl)[CH:30]=3)N=2)CC1.[O:37]=P(Cl)(Cl)Cl.[C:42](#[N:44])[CH3:43]>>[CH:16]1([C:4]2[N:3]=[C:2]([NH:44][CH2:42][C@@H:43]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[OH:37])[CH:7]=[C:6]([C:8]3[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([Cl:15])[CH:9]=3)[N:5]=2)[CH2:18][CH2:17]1

Participants

5

Reactant 4

HCID 6342AcetonitrileHCID 24813Phosphorus oxychlorideHCID 809526634-Chloro-2-cyclopropyl-6-(3,4-dichloro-phenyl)-PyrimidineHCID 178515609HCID 178515609, compound

Product 1

HCID 44205060(1R)-2-{[2-Cyclopropyl-6-(3,4-dichlorophenyl)pyrimidin-4-yl]amino}-1-phenylethanolYield 81%

Conditions

Temperature
80 °C

Procedure

4-Chloro-2-cyclopropyl-6-(3,4-dichloro-phenyl)-Pyrimidine. To a suspension of 2-cyclopropyl-6-(3,4-dichloro-phenyl)-pyrimidin-4-ol (131 mg, 0.467 mmol) in acetonitrile was added POCl3 (0.13 mL, 1.42 mmol). The reaction mixture was heated at 80° C. for 105 min, cooled to rt, quenched with satd. aq. NaHCO3, and extracted with EtOAc. The organic layer was dried (Na2SO4) and concentrated. The crude residue was purified (FCC) to give the title compound (113 mg, 81%).

Workup

  1. temperaturecooled to rt
  2. customquenched with satd
  3. extractionaq. NaHCO3, and extracted with EtOAc
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. concentrationconcentrated
  6. customThe crude residue was purified (FCC)

Sources & evidence

ORD record
ord-b617f4ecac064816ba54657d852b0717
Source dataset
uspto-grants-2013_12
Patent number
US08598202B2

Reaction notes

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