Phosphorus oxychloride → HCID 17963002, compound

HRID 1592929Notes

Reaction equation

HRID 1592929 reaction equation
O[C:2]1[C:3]2[CH:10]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=3)[O:8][C:4]=2[N:5]=[CH:6][N:7]=1.P(Cl)(Cl)([Cl:22])=O>>[Cl:22][C:2]1[C:3]2[CH:10]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=3)[O:8][C:4]=2[N:5]=[CH:6][N:7]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178526515HCID 178526515, compound

Product 1

HCID 17963002HCID 17963002, compound

Procedure

13.5 g of 4-hydroxy-6-(4-nitrophenyl)furo[2,3-d]pyrimidine are heated for 1.5 h under RF in ca. 200 ml of phosphorus oxychloride (Fluka, Buchs). Afterwards, the reaction mixture is left to stand in the open for 3 days, and then added to 4 kg of ice. The suspension is filtered by suction and washed with a lot of H2O. The product is sublimated at ca. 200° C. and at ca. 0.1 mbar. The sublimate consists of lemon-yellow non-crystalline needles: m.p.: from 245° C. (decomposition). 1H-NMR (300 MHz, DMSO): 8.91 (s, H—C(2)); 8.40, 8.31 (d, J=9.2, H—C(2′, 3′)); 8.09 (s, H—C(5)).

Workup

  1. waitAfterwards, the reaction mixture is left
  2. customopen for 3 days
  3. filtrationThe suspension is filtered by suction
  4. washwashed with a lot of H2O
  5. customis sublimated at ca. 200° C. and at ca. 0.1 mbar

Sources & evidence

ORD record
ord-3ae59d3349564fc3b114305894e4e490
Source dataset
uspto-grants-2007_11
Patent number
US07294633B2

Reaction notes

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