1,1'-Carbonyldiimidazole → (2,4-dioxo-1,4-dihydro-2H-pyrido[3,4-d]pyrimidin-3-yl)-acetic acid methyl ester

HRID 1887188Notes

Reaction equation

HRID 1887188 reaction equation
[CH3:1][O:2][C:3](=[O:15])[CH2:4][NH:5][C:6]([C:8]1[CH:13]=[CH:12][N:11]=[CH:10][C:9]=1[NH2:14])=[O:7].[C:16](N1C=CN=C1)(N1C=CN=C1)=[O:17].N12CCCN=C1CCCCC2>O1CCCC1>[CH3:1][O:2][C:3](=[O:15])[CH2:4][N:5]1[C:6](=[O:7])[C:8]2[CH:13]=[CH:12][N:11]=[CH:10][C:9]=2[NH:14][C:16]1=[O:17]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 67501539[(3-Amino-pyridine-4-carbonyl)-amino]-acetic acid methyl ester

Product 1

HCID 67502666(2,4-dioxo-1,4-dihydro-2H-pyrido[3,4-d]pyrimidin-3-yl)-acetic acid methyl esterYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 100 mg of [(3-amino-pyridine-4-carbonyl)-amino]-acetic acid methyl ester in tetrahydrofuran (4.5 mL) is added 194 mg of 1,1′-carbonyldiimidazole and 0.18 mL of 1,8-diazabicyclo[5.4.0]undec-7-ene at room temperature and the mixture is stirred at the same temperature for 2 h. Then the solvent is removed under vacuum and the residue is purified by flash chromatography on silica gel to give 100 mg (89%) of (2,4-dioxo-1,4-dihydro-2H-pyrido[3,4-d]pyrimidin-3-yl)-acetic acid methyl ester.

Workup

  1. customThen the solvent is removed under vacuum
  2. customthe residue is purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-a7200eb155e649f3bbc640f566912017
Source dataset
uspto-grants-2013_08
Patent number
US08501749B2

Reaction notes

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