Phosphorus oxychloride → HCID 59380405, compound

HRID 2353832Notes

Reaction equation

HRID 2353832 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[C:8]3[C:13](=O)[NH:12][CH:11]=[N:10][C:9]=3[S:15][C:4]=2[CH:3]=1.O=P(Cl)(Cl)[Cl:18]>C(N(CC)CC)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[C:8]3[C:13]([Cl:18])=[N:12][CH:11]=[N:10][C:9]=3[S:15][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 59380494HCID 59380494, compound

Product 1

HCID 59380405HCID 59380405, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

7-Bromo[1]benzothieno[2,3-d]pyrimidin-4(3H)-one (7.80 g, 27.7 mmol), POCl3 (70 mL) and triethylamine (70 mL) were heated in an oil bath at 80° C. for 3 h. The resulting slurry was concentrated on a rotavap, slurried in dichloromethane and poured into 500 mL of satd NaHCO3. The organic phase was then washed with satd NaHCO3, water, and then collected. The initial aqueous phase (pH<1) was basified with 1.0 N NaOH and extracted with dichloromethane. The organic layers were combined, dried with sodium sulfate, filtered, and concentrated under high vacuum to yield a crude brown solid (7.6 g, 91%). 1H NMR (DMSO-d6) δ 9.05 (s, 1H), 8.60 (d, 1H), 8.60 (s, 1H), 7.88 (d, 1H).

Workup

  1. concentrationThe resulting slurry was concentrated on a rotavap
  2. additionpoured into 500 mL of satd NaHCO3
  3. washThe organic phase was then washed with satd NaHCO3, water
  4. customcollected
  5. extractionextracted with dichloromethane
  6. dry with materialdried with sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under high vacuum

Sources & evidence

ORD record
ord-e554737f2e1143eba523f17c1345dd93
Source dataset
uspto-grants-2010_07
Patent number
US07750017B2

Reaction notes

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