2-Aminopyridine-3-carboxamide → HCID 135899199, compound

HRID 2100505Notes

Reaction equation

HRID 2100505 reaction equation
[NH2:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].CO[C:13](=O)[CH2:14][O:15][CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH3:25])[CH:19]=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C>C1COCC1>[CH3:25][O:24][C:20]1[CH:19]=[C:18]([CH2:17][CH2:16][O:15][CH2:14][C:13]2[NH:6][C:4](=[O:5])[C:3]3[CH:7]=[CH:8][CH:9]=[N:10][C:2]=3[N:1]=2)[CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 5066232-Aminopyridine-3-carboxamideHCID 2733832Lithium HexamethyldisilazideHCID 68567426HCID 68567426, compound

Product 1

HCID 135899199HCID 135899199, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In analogy to example 91.3, 2-amino-nicotinamide and [2-(3-methoxy-phenyl)-ethoxy]-acetic acid methyl ester (prepared from 2-(3-methoxyphenyl)ethanol [5020-41-7] in analogy to example 91.1-91.2) reacted in the presence of LiHMDS in THF to yield after purification of the crude product with column chromatography (silica gel, EtOAc) 2-[2-(3-methoxy-phenyl)-ethoxymethyl]-3H-pyrido[2,3-d]pyrimidin-4-one as white solid. MS (m/e): 312.2 [M+H+].

Workup

  1. customto yield
  2. customafter purification of the crude product with column chromatography (silica gel, EtOAc) 2-[2-(3-methoxy-phenyl)-ethoxymethyl]-3H-pyrido[2,3-d]pyrimidin-4-one as white solid

Sources & evidence

ORD record
ord-bb5b4843a515432da8cae501e6be6b50
Source dataset
uspto-grants-2009_08
Patent number
US07572801B2

Reaction notes

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