Water → 2-Amino-N-benzyl-6-(2-furyl)pyrimidine-4-carboxamide

HRID 254159

Reaction equation

HRID 254159 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]([OH:10])=O)[CH:5]=[C:4]([C:11]2[O:12][CH:13]=[CH:14][CH:15]=2)[N:3]=1.[CH2:16]([NH2:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.CCN=C=NCCCN(C)C.Cl.O>CN(C=O)C.CN(C)C1C=CN=CC=1>[NH2:1][C:2]1[N:7]=[C:6]([C:8]([NH:23][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:10])[CH:5]=[C:4]([C:11]2[O:12][CH:13]=[CH:14][CH:15]=2)[N:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7504BenzylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 287995992-Amino-6-(2-furyl)pyrimidine-4-carboxylic acid

Product 1

HCID 452679872-Amino-N-benzyl-6-(2-furyl)pyrimidine-4-carboxamideYield 40%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 2-amino-6-(2-furyl)pyrimidine-4-carboxylic acid (103 mg, 0.5 mmol) in DMF (2 mL) was treated with benzylamine (59 mg, 0.55 mmol), EDCl (104 mg, 0.54 mmol) and 4-dimethylaminopyridine (66 mg, 0.54 mmol), stirred at room temperature for 17 h, poured into water (25 mL) and extracted with EtOAc (2×25 mL). The combined organic phase was washed with water (25 mL), dried (MgSO4), concentrated in vacuo and purified by chromatography [SiO2; isopropyl ether:EtOAc, (100:0-0:100)] to give the title compound (52 mg, 40%) as an off-white solid.

Workup

  1. extractionextracted with EtOAc (2×25 mL)
  2. washThe combined organic phase was washed with water (25 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. custompurified by chromatography [SiO2; isopropyl ether:EtOAc, (100:0-0:100)]

Sources & evidence

ORD record
ord-2285890de6b1449bbec46ed0cb90b966
Source dataset
uspto-grants-2011_01
Patent number
US07875600B2

Linked notes

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