Acrylic Acid → N-(3-(4-(phenylthio)pyrimidin-2-ylamino)phenyl)acrylamide

HRID 81717Notes

Reaction equation

HRID 81717 reaction equation
[C:1]1([S:7][C:8]2[CH:13]=[CH:12][N:11]=[C:10]([NH:14][C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([NH2:21])[CH:16]=3)[N:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:22](O)(=[O:25])[CH:23]=[CH2:24].Cl.CN(C)CCCN=C=NCC.C(N(CC)CC)C.N1(C2C=CN=CC=2)CCCC1>ClCCl>[C:1]1([S:7][C:8]2[CH:13]=[CH:12][N:11]=[C:10]([NH:14][C:15]3[CH:16]=[C:17]([NH:21][C:22](=[O:25])[CH:23]=[CH2:24])[CH:18]=[CH:19][CH:20]=3)[N:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 5

HCID 6581Acrylic AcidHCID 8471TriethylamineHCID 755674-PyrrolidinopyridineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68746426N1-(4-(phenylthio)pyrimidin-2-yl)benzene-1,3-diamine

Product 1

HCID 59491563N-(3-(4-(phenylthio)pyrimidin-2-ylamino)phenyl)acrylamideYield 33%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of N1-(4-(phenylthio)pyrimidin-2-yl)benzene-1,3-diamine (80 mg, 0.27 mmol) and acrylic acid (37 μL, 0.54 mmol) in anhydrous dichloromethane (2 mL), was added 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride salt (78 mg, 0.41 mmol), triethylamine (114 μL, 0.82 mmol) and 4-pyrrolidinopyridine (5 mg). The resulting mixture was stirred at room temperature under nitrogen atmosphere for 16 hours. It was diluted with dichloromethane (20 mL), washed with water, 2.0 Maqueous sodium carbonate solution, and dried (Na2SO4). After removal of the solvent in vacuo, the residue was flash chromatographed on silica gel using ethyl acetate:petroleum ether (50:50→100:0) as eluant to give the desired product (31 mg, 33%).

Workup

  1. washwashed with water, 2.0 Maqueous sodium carbonate solution
  2. dry with materialdried (Na2SO4)
  3. customAfter removal of the solvent in vacuo
  4. customchromatographed on silica gel

Sources & evidence

ORD record
ord-8ed5f0d69e874edf8a480bbff42c6d10
Source dataset
uspto-grants-2014_09
Patent number
US08846704B2

Reaction notes

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