Dimethyl Sulfoxide → 1-Cyclopropyl-3-[4-(6-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-yloxy)phenyl]urea

HRID 387784Notes

Reaction equation

HRID 387784 reaction equation
[CH:1]1([NH:4][C:5](=O)[O:6]C2C=CC=CC=2)[CH2:3][CH2:2]1.CS(C)=O.[C:18]1([C:24]2[NH:40][C:27]3[N:28]=[CH:29][N:30]=[C:31]([O:32][C:33]4[CH:38]=[CH:37][C:36]([NH2:39])=[CH:35][CH:34]=4)[C:26]=3[CH:25]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>O>[CH:1]1([NH:4][C:5]([NH:39][C:36]2[CH:37]=[CH:38][C:33]([O:32][C:31]3[C:26]4[CH:25]=[C:24]([C:18]5[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=5)[NH:40][C:27]=4[N:28]=[CH:29][N:30]=3)=[CH:34][CH:35]=2)=[O:6])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 13648483Phenyl cyclopropylcarbamateHCID 589311894-(6-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-yloxy)phenylamine

Product 1

HCID 589314631-Cyclopropyl-3-[4-(6-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-yloxy)phenyl]ureaYield 11.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

After adding 30 mg of phenyl cyclopropylcarbamate and 0.5 ml of dimethylsulfoxide to 40 mg of 4-(6-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-yloxy)phenylamine, the mixture was stirred at 80° C. for 4 hours. The mixture was returned to room temperature, water was added, liquid separation and extraction were performed with ethyl acetate, and the solid obtained by concentration to dryness was washed with ether to obtain 6 mg of the title compound.

Workup

  1. customwas returned to room temperature
  2. customliquid separation and extraction
  3. customthe solid obtained by concentration to dryness
  4. washwas washed with ether

Sources & evidence

ORD record
ord-5c4b925d178e462b98a0db4e3ee66372
Source dataset
uspto-grants-2013_02
Patent number
US08372981B2

Reaction notes

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