Phosphorus oxychloride → HCID 21906820, compound

HRID 1005798Notes

Reaction equation

HRID 1005798 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[N:22]=[CH:21][N:20]=[C:19](O)[CH:18]=2)=[CH:13][C:12]=1[C:24]([F:27])([F:26])[F:25])([CH3:3])[CH3:2].O=P(Cl)(Cl)[Cl:30]>>[Cl:30][C:19]1[CH:18]=[C:17]([C:14]2[CH:15]=[CH:16][C:11]([S:10][C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[CH:1]([CH3:3])[CH3:2])=[C:12]([C:24]([F:26])([F:25])[F:27])[CH:13]=2)[N:22]=[CH:21][N:20]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178438985HCID 178438985, compound

Product 1

HCID 21906820HCID 21906820, compoundYield 51%

Procedure

Then, 4-chloro-6-(4-(2-isopropyl-phenylsulfanyl)-3-trifluoromethyl-phenyl)-pyrimidine 47 was prepared as follows. Compound 46 (1.40 g, 3.59 mmol) was treated with POCl3 (30 mL) at 60° C. for an hour. The reaction mixture was concentrated on a rotor-vapor, and the residue was treated with crushed ice (10 g). Water (50 mL) was added. The aqueous solution was then extracted with ethyl acetate (2×50 mL). The combined organic layers were washed with brine (3×50 mL), dried over MgSO4, filtered and concentrated. The crude product was purified by chromatography to give a brown oil 47 (0.74 g, 51%). 1H-NMR (CDCl3, 400 MHz) δ 1.19 (d, J=6.7 Hz, 6H), 3.50 (heptet, J=6.8 Hz, 1H), 6.89 (d, J=8.5 Hz, 1H), 7.24-7.28 (m, 1H), 7.46-7.50 (m, 2H), 7.54 (d, J=7.6 Hz, 1H), 7.68 (s, 1H), 7.93 (d, J=8.4 Hz, 1H), 8.38 (s, 1H), 9.00(s, 1H), MS (DCI) m/z 409, 411 (M+H)+.

Workup

  1. customThen, 4-chloro-6-(4-(2-isopropyl-phenylsulfanyl)-3-trifluoromethyl-phenyl)-pyrimidine 47 was prepared
  2. concentrationThe reaction mixture was concentrated on a rotor-vapor
  3. additionthe residue was treated with crushed ice (10 g)
  4. additionWater (50 mL) was added
  5. extractionThe aqueous solution was then extracted with ethyl acetate (2×50 mL)
  6. washThe combined organic layers were washed with brine (3×50 mL)
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude product was purified by chromatography

Sources & evidence

ORD record
ord-4ba5d3b2c89448319d92430df666cd06
Source dataset
uspto-grants-2004_09
Patent number
US06787542B2

Reaction notes

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