Benzenepentanoic acid → 5-Phenyl-pentanoic acid (5-cyano-pyrimidin-4-yl)-amide

HRID 2076810Notes

Reaction equation

HRID 2076810 reaction equation
C(Cl)(=O)C(Cl)=O.[C:7]1([CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=O)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[NH2:20][C:21]1[C:26]([C:27]#[N:28])=[CH:25][N:24]=[CH:23][N:22]=1>C(Cl)Cl.CN(C=O)C.N1C=CC=CC=1>[C:27]([C:26]1[C:21]([NH:20][C:17](=[O:19])[CH2:16][CH2:15][CH2:14][CH2:13][C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[N:22][CH:23]=[N:24][CH:25]=1)#[N:28]

Participants

7

Reactant 3

HCID 16757Benzenepentanoic acidHCID 65578Oxalyl chlorideHCID 7372084-Amino-5-pyrimidinecarbonitrile

Product 1

HCID 670991235-Phenyl-pentanoic acid (5-cyano-pyrimidin-4-yl)-amideYield 84.8%

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

Under an atmosphere of nitrogen, oxalyl chloride (961 mg) was added dropwise to a solution of 5-phenylvaleric acid (Fluka, 1.00 g) in CH2Cl2 (8 ml) and DMF (0.4 ml). After stirring at ambient temperature overnight, the mixture was slowly added at 0° C. to a solution of 4-aminopyrimidine-5-carbonitrile (Aldrich, 505 mg) in pyridine (8 ml). The mixture was stirred overnight at r.t., taken up in CH2Cl2, washed with water, and dried (Na2SO4). After filtration, the solvent was evaporated, and the title compound (1.00 g, 64%) was obtained from the residue by column chromatography (silica gel, eluent gradient n-heptane/ethyl acetate=100:0-60:40). MS: m/e=281.3 [M+H+]. 1H NMR (d6-DMSO): δ 1.60-1.80 (m, 4H), 2.55-2.60 (m, 2H), 3.14 (t, 2H), 7.14-7.29 (m, 5H), 9.17 (d, 2H), 11.34 (bs, 1H).

Workup

  1. stirringThe mixture was stirred overnight at r.t.
  2. washwashed with water
  3. dry with materialdried (Na2SO4)
  4. filtrationAfter filtration
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-fc0486f837ba4792a85e157614a6b608
Source dataset
uspto-grants-2011_04
Patent number
US07928106B2

Reaction notes

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