4-chloro-6-(pyrid-2-yl)-7H-pyrrolo[2,3-d]pyrimidine → 4-(3-Chloro-anilino)-6-(pyrid-2-yl)-7H-pyrrolo[2,3-d]pyrimidine

HRID 369833Notes

Reaction equation

HRID 369833 reaction equation
[Cl:1][C:2]1[C:3]2[CH:10]=[C:9]([C:11]3[CH:16]=CC=C[N:12]=3)NC=2N=CN=1.[N:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:23]1[NH:32][C:26]2[N:27]=[CH:28][N:29]=[C:30](O)[C:25]=2[CH:24]=1>P(Cl)(Cl)(Cl)=O>[Cl:1][C:2]1[CH:16]=[C:11]([CH:9]=[CH:10][CH:3]=1)[NH:12][C:30]1[C:25]2[CH:24]=[C:23]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][N:17]=3)[NH:32][C:26]=2[N:27]=[CH:28][N:29]=1

Participants

4

Reactant 2

HCID 232826944-chloro-6-(pyrid-2-yl)-7H-pyrrolo[2,3-d]pyrimidineHCID 178518054HCID 178518054, compound

Product 1

HCID 99490364-(3-Chloro-anilino)-6-(pyrid-2-yl)-7H-pyrrolo[2,3-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

4-Chloro-6-(pyrid-2-yl)-7H-pyrrolo[2,3-d]pyrimidine With the exclusion of moisture, 7.05 g (33.2 mmol) of 6-(pyrid-2-yl)-7H-pyrrolo[2,3-d]-pyrimidin-4-ol and 70 ml of phosphorus oxychloride are heated at boiling for 2 hours. The dark-brown suspension is concentrated by evaporation to a residual volume of 20 ml. The residue is introduced in portions into water, neutralized with solid NaHCO3 and 0.2 liter of ethyl acetate is added thereto. Filtering and washing with hot THF yield the title compound; 1H-NMR (300 MHz, DMSO-d6): 13.2 (sb, 1H), 8.72 (d, J=7, 1H), 8.63 (s, 1H), 8.23 (d, J=11, 1H), 7.97 (t, J=11, 1H), 7.46 (dd, J,=7, J2 =11, 1H), 7.35 (s, 1H). Further product can be isolated from the filtrate and the THF washing solution, which is concentrated by evaporation, by partitioning between ethyl acetate/water and digesting in ethyl acetate/diethyl ether.

Workup

  1. concentrationThe dark-brown suspension is concentrated by evaporation to a residual volume of 20 ml
  2. additionThe residue is introduced in portions into water
  3. additionis added
  4. filtrationFiltering
  5. washwashing with hot THF

Sources & evidence

ORD record
ord-d0ac2c40097d44a69300cc73fd055478
Source dataset
uspto-grants-2000_10
Patent number
US06140332

Reaction notes

Loading…