Water → HCID 53348079, compound

HRID 2046302Notes

Reaction equation

HRID 2046302 reaction equation
Cl[C:2]1[C:3]2[CH:10]=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[N+:11]([C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1)([O-:13])=[O:12].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[N+:11]([C:14]1[CH:19]=[CH:18][C:17]([O:20][C:2]2[C:3]3[CH:10]=[CH:9][NH:8][C:4]=3[N:5]=[CH:6][N:7]=2)=[CH:16][CH:15]=1)([O-:13])=[O:12]

Participants

6

Reactant 4

HCID 962WaterHCID 9804-NitrophenolHCID 11430Potassium CarbonateHCID 53566827H-Pyrrolo(2,3-d)pyrimidine, 4-chloro-

Product 1

HCID 53348079HCID 53348079, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine (3.1 g, 20 mmol) dissolved in DMF (60 ml) are added 4-nitrophenol (4.9 g, 35 mmol) and potassium carbonate (5.3 g, 38 mmol). The resulting solution is heated to 110° C. overnight. After the completion of reaction as indicated by disappearance of starting material, the reaction mixture is cooled to ambient temperature and poured into cold water. The resulting solids are collected by filtration and washed with water (3×100 ml). The crude product is purified by flash column chromatography using hexanes:ethyl acetate (1/1 v/v) as eluent to afford the title compound as a solid: 1H NMR 400 MHz (DMSO-d6) δ 12.34 (bs, 1H), 8.35 (m, 3H), 7.57 (m, 3H), 6.61 (m, 1H); HRMS (MALDI-FTMS) calculated for C12H9N4O3 [MH]+ 257.0669,found 257.0670.

Workup

  1. customAfter the completion of reaction
  2. temperaturethe reaction mixture is cooled to ambient temperature
  3. filtrationThe resulting solids are collected by filtration
  4. washwashed with water (3×100 ml)
  5. customThe crude product is purified by flash column chromatography

Sources & evidence

ORD record
ord-322b24bd8c6d47bf9c3bd01da4a0b15b
Source dataset
uspto-grants-2013_11
Patent number
US08592433B2

Reaction notes

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