Phosphorus oxychloride → 4-Chloro-6-phenylfuro[2,3-d]pyrimidine

HRID 2408976Notes

Reaction equation

HRID 2408976 reaction equation
[C:1]1([C:7]2[O:16][C:10]3[N:11]=[CH:12][NH:13][C:14](=O)[C:9]=3[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O=P(Cl)(Cl)[Cl:19]>>[Cl:19][C:14]1[C:9]2[CH:8]=[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[O:16][C:10]=2[N:11]=[CH:12][N:13]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 580167996-phenylfuro[2,3-d]pyrimidin-4(3H)-one

Product 1

HCID 579464884-Chloro-6-phenylfuro[2,3-d]pyrimidineYield 74%

Conditions

Temperature
60 °C

Procedure

A mixture of 6-phenylfuro[2,3-d]pyrimidin-4(3H)-one (1.0 g) and POCl3 (10 mL) was stirred at 55-65° C. for 3 h. The reaction mixture was poured into ice cold water and stirred for 10 min. The solution was extracted with chloroform (3×100 mL) and the combined chloroform layer was washed with aq. NaHCO3 solution, water, brine and dried over sodium sulfate. The residue was chromatographed over silica gel column using hexane-EtOAc (95:5) as eluents to give the product as a white color solid (800 mg, 74%), mp 136-138° C. 1H NMR (400 MHz, CDCl3): δ 8.74 (1H, s), 7.90-7.93 (2H, m), 7.45-7.54 (3H, m), 7.08 (1H, s).

Workup

  1. additionThe reaction mixture was poured into ice cold water
  2. stirringstirred for 10 min
  3. extractionThe solution was extracted with chloroform (3×100 mL)
  4. washthe combined chloroform layer was washed with aq. NaHCO3 solution, water, brine
  5. dry with materialdried over sodium sulfate
  6. customThe residue was chromatographed over silica gel column

Sources & evidence

ORD record
ord-10807ee8d23149ff95cb5f2720371fa2
Source dataset
uspto-grants-2014_08
Patent number
US08815879B2

Reaction notes

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