Phosphorus oxychloride → 7-benzyl-4-chloro-5,6-dimethylpyrrolo[2,3-d]pyrimidine

HRID 2293119Notes

Reaction equation

HRID 2293119 reaction equation
O[C:2]1[C:3]2[C:10]([CH3:11])=[C:9]([CH3:12])[N:8]([CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:4]=2[N:5]=[CH:6][N:7]=1.O=P(Cl)(Cl)[Cl:22]>>[Cl:22][C:2]1[C:3]2[C:10]([CH3:11])=[C:9]([CH3:12])[N:8]([CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178428435HCID 178428435, compound

Product 1

HCID 14754767-benzyl-4-chloro-5,6-dimethylpyrrolo[2,3-d]pyrimidine

Procedure

2.5 g of 4-hydroxy-5,6-dimethyl-7-benzyl-pyrrolo[2,3-d]pyrimidine are boiled at reflux with 20 ml of POCl3 for 2.5 hours. The brown solution is cooled to RT and poured onto ice-water. The brownish precipitate is filtered off with suction and dissolved in ethyl acetate. The ethyl acetate phase is washed with water, dried and concentrated in a rotary evaporator until white crystals form. 4-Chloro-5,6-dimethyl-7-benzyl-pyrrolo[2,3-d]-pyrimidine is obtained in the form of white crystals having a melting point of 115°-116° C.

Workup

  1. additionpoured onto ice-water
  2. filtrationThe brownish precipitate is filtered off with suction
  3. dissolutiondissolved in ethyl acetate
  4. washThe ethyl acetate phase is washed with water
  5. customdried
  6. concentrationconcentrated in a rotary evaporator until white crystals form

Sources & evidence

ORD record
ord-c14bc5c43c9b4f72908b8edcec6f26f3
Source dataset
uspto-grants-1997_11
Patent number
US05686457

Reaction notes

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