Triethyl phosphite → 6H-Pyrimido(2',1':2,3)imidazo(4,5-b)indole

HRID 127351Notes

Reaction equation

HRID 127351 reaction equation
[N:1]([C:3]1[N:7]2[CH:8]=[CH:9][CH:10]=[N:11][C:6]2=[N:5][C:4]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=O.C(OP(OCC)OCC)C>C1(C)C=CC=CC=1>[N:11]1[C:6]2=[N:5][C:4]3[C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=4[NH:1][C:3]=3[N:7]2[CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 31215Triethyl phosphite2×HCID 2539243-Nitroso-2-phenylimidazo(1,2-a)pyrimidine

Product 1

HCID 3388896H-Pyrimido(2',1':2,3)imidazo(4,5-b)indole

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 9.0 g of analytically pure 3-nitroso-2-phenylimidazo(1,2-a)pyrimidine (0.04 mol) and 10 ml of 97% triethylphosphite (0.05 mol) in 50 ml of anhydrous toluene is refluxed for 1 hour with stirring and under a constant flow of dry nitrogen gas. The temperature of the oil bath is kept between 110° and 120° C. After cooling the solvent and excess triethylphosphite are removed by vacuum distillation at 0.2 Torr. The temperature of the oil bath was kept under 120° C. during the distillation. The residue, which is a thick liquid, is kept overnight at 0° C. during which time it solidifies. The solid is washed on a glass filter with cold carbon tetrachloride and then recrystallized from CCl4. Yield about 5 g, m.p. 96° to 98° C.

Workup

  1. temperatureis refluxed for 1 hour
  2. customis kept between 110° and 120° C
  3. customare removed by vacuum distillation at 0.2 Torr
  4. distillationThe temperature of the oil bath was kept under 120° C. during the distillation
  5. washThe solid is washed on a glass
  6. filtrationfilter with cold carbon tetrachloride
  7. customrecrystallized from CCl4

Sources & evidence

ORD record
ord-5eadb82fe9dd401d92cf41d6281c48c9
Source dataset
uspto-grants-1981_03
Patent number
US04255573

Reaction notes

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