Aniline → 2-(4-Fluorophenyl)-N-phenyl-5-pyrimidinecarboxamide

HRID 219645Notes

Reaction equation

HRID 219645 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[CH:12][C:11]([C:14]([OH:16])=O)=[CH:10][N:9]=2)=[CH:4][CH:3]=1.O[N:18]1[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2N=N1.C1CCC(N=C=NC2CCCCC2)CC1.NC1C=CC=CC=1.C(O)C(N)(CO)CO>CN(C=O)C>[C:22]1([NH:18][C:14]([C:11]2[CH:12]=[N:13][C:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)=[N:9][CH:10]=2)=[O:16])[CH:23]=[CH:24][CH:25]=[CH:26][CH:21]=1

Participants

7

Reactant 5

HCID 6115AnilineHCID 6503Tris(hydroxymethyl)aminomethaneHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 176063482-(4-Fluorophenyl)pyrimidine-5-carboxylic acid

Product 1

HCID 166664162-(4-Fluorophenyl)-N-phenyl-5-pyrimidinecarboxamideYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-(4-fluoro-phenyl)-pyrimidine-5-carboxylic acid (107 mg, 0.49 mmol, prepared according to the general procedure described in Example 2, steps 1 and 2), 1-hydroxybenzotriazole (75 mg, 0.56 mmol) and PS-DCC (511 mg, 1.28 mmol/g, 0.65 mmol) in DMF (8 mL) is shaken at room temperature for 15 min. Aniline (30.4 mg, 0.33 mmol) is added. The mixture is shaken at room temperature for 18 hours. PS-trisamine (392 mg, 3.75 mmol/g, 1.47 mmol) is added and the mixture is continually shaken at room temperature for 18 hours. The solid is filtered and washed with EtOAc. The filtrate is concentrated to afford 2-(4-fluoro-phenyl)-pyrimidine-5-carboxylic acid phenylamide (83.4 mg, 86%) as a solid. MS: 294 (M+H).

Workup

  1. customprepared
  2. stirringThe mixture is shaken at room temperature for 18 hours
  3. stirringthe mixture is continually shaken at room temperature for 18 hours
  4. filtrationThe solid is filtered
  5. washwashed with EtOAc
  6. concentrationThe filtrate is concentrated

Sources & evidence

ORD record
ord-d8ec1f9450094eab8acb6a02a3da163c
Source dataset
uspto-grants-2012_06
Patent number
US08202863B2

Reaction notes

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