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

HRID 387781
Notes
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Reaction equation

HRID 387781 reaction equation
[C:1]1([C:7]2[NH:23][C:10]3[N:11]=[CH:12][N:13]=[C:14]([O:15][C:16]4[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][CH:17]=4)[C:9]=3[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:24][C:25]1[CH:30]=[CH:29][C:28]([N:31]=[C:32]=[O:33])=[CH:27][CH:26]=1>C1(C)C=CC=CC=1.C(#N)C>[F:24][C:25]1[CH:30]=[CH:29][C:28]([NH:31][C:32]([NH:22][C:19]2[CH:20]=[CH:21][C:16]([O:15][C:14]3[C:9]4[CH:8]=[C:7]([C:1]5[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=5)[NH:23][C:10]=4[N:11]=[CH:12][N:13]=3)=[CH:17][CH:18]=2)=[O:33])=[CH:27][CH:26]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 709554-Fluorophenyl isocyanateHCID 589311894-(6-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-yloxy)phenylamine

Product 1

HCID 589314531-(4-Fluorophenyl)-3-[4-(6-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-yloxy)phenyl]urea

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6342AcetonitrileSolvent

Procedure

After dissolving 40 mg of 4-(6-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-yloxy)phenylamine in 4.5 ml of toluene and 4.5 ml of acetonitrile at 110° C., 4-fluorophenyl isocyanate (16.6 μl) was added and the mixture was stirred for 1 hour. After returning the mixture to room temperature, the precipitated crystals were filtered out and dried to obtain 37 mg of the title compound.

Workup

  1. customto room temperature
  2. filtrationthe precipitated crystals were filtered out
  3. customdried

Sources & evidence

ORD record
ord-c959a7438e7d44838214b4f1f21bc953
Source dataset
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08372981B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes