Phosphorus oxychloride → HCID 57614141, compound

HRID 1674709Notes

Reaction equation

HRID 1674709 reaction equation
Cl.[F:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:14](=[O:15])[C:13]3[N:16]=[CH:17][S:18][C:12]=3[N:11]=[C:10]2S)=[CH:5][CH:4]=1.O=P(Cl)(Cl)[Cl:22]>C(Cl)Cl>[Cl:22][C:10]1[N:9]([C:6]2[CH:7]=[CH:8][C:3]([F:2])=[CH:4][CH:5]=2)[C:14](=[O:15])[C:13]2[N:16]=[CH:17][S:18][C:12]=2[N:11]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178479611HCID 178479611, compound

Product 1

HCID 57614141HCID 57614141, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
135 °C

Procedure

6-(4-Fluorophenyl)-5-mercapto[1,3]thiazolo[5,4-d]pyrimidin-7(6H)-one hydrochloride (0.2 g, 0.633 mmol) is added to POCl3 (10 mL), and the resulting solution is refluxed at 135° C. for 41 h. Most of the volatiles are removed under reduced pressure and the residual solvent is co-evaporated with toluene (50 mL×3). The dark solid obtained is dissolved in CH2Cl2 (200 mL) and washed with saturated NaHCO3 solution (100 mL×5), brine (50 mL×2), and dried over MgSO4. After removing solvent, silica gel column chromatography (EtOAc:hexanes=50:50) yields the title compound as a yellow solid. 1H NMR (400 MHz, CDCl3) 8.88 (1H, s), 7.26 (4H, m).

Workup

  1. customMost of the volatiles are removed under reduced pressure
  2. customThe dark solid obtained
  3. washwashed with saturated NaHCO3 solution (100 mL×5), brine (50 mL×2)
  4. dry with materialdried over MgSO4
  5. customAfter removing solvent, silica gel column chromatography (EtOAc:hexanes=50:50)

Sources & evidence

ORD record
ord-5d34fe93cf43465882b1abc569f6913c
Source dataset
uspto-grants-2011_08
Patent number
US08003656B2

Reaction notes

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