Aniline → 2-Pyridin-4-yl-pyrimidine-5-carboxylic acid phenylamide

HRID 219640Notes

Reaction equation

HRID 219640 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[N:12]=[CH:11][C:10]([C:13]([OH:15])=O)=[CH:9][N:8]=2)=[CH:3][CH:2]=1.O[N:17]1[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2N=N1.C1CCC(N=C=NC2CCCCC2)CC1.NC1C=CC=CC=1.C(O)C(N)(CO)CO>CN(C=O)C>[C:21]1([NH:17][C:13]([C:10]2[CH:11]=[N:12][C:7]([C:4]3[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=3)=[N:8][CH:9]=2)=[O:15])[CH:22]=[CH:23][CH:24]=[CH:25][CH:20]=1

Participants

7

Reactant 5

HCID 6115AnilineHCID 6503Tris(hydroxymethyl)aminomethaneHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 227102132-(Pyridin-4-yl)pyrimidine-5-carboxylic acid

Product 1

HCID 166664122-Pyridin-4-yl-pyrimidine-5-carboxylic acid phenylamideYield 16%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-pyridin-4-yl-pyrimidine-5-carboxylic acid (100 mg, 0.5 mmol), 1-hydroxybenzotriazole (76.1 mg, 0.56 mmol) and PS-DCC (539 mg, 1.25 mmol/g, 0.66 mmol) in DMF (8 mL) is shaken at room temperature for 15 min, and aniline (31 mg, 0.33 mmol) is added. After shaking at room temperature for 18 hours, PS-trisamine (398 mg, 3.75 mmol/g, 1.49 mmol) is added and the mixture is continually shaken at room temperature for 18 hours. The solid is filtered and washed with DCM. The filtrate is concentrated to yield 2-pyridin-4-yl-pyrimidine-5-carboxylic acid phenylamide (15 mg, 16%) as solid. MS: 277 (M+H).

Workup

  1. stirringAfter shaking at room temperature for 18 hours
  2. stirringthe mixture is continually shaken at room temperature for 18 hours
  3. filtrationThe solid is filtered
  4. washwashed with DCM
  5. concentrationThe filtrate is concentrated

Sources & evidence

ORD record
ord-e52338bb2fe74e63bc3bfa1e4ebf85ca
Source dataset
uspto-grants-2012_06
Patent number
US08202863B2

Reaction notes

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