Water → 6-acetyl-2-[4-(1,3-oxazol-5-yl)anilino]-1,5,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-one

HRID 1930571Notes

Reaction equation

HRID 1930571 reaction equation
[O:1]1[C:5]([C:6]2[CH:11]=[CH:10][C:9]([NH:12][C:13]([NH2:15])=[NH:14])=[CH:8][CH:7]=2)=[CH:4][N:3]=[CH:2]1.[C:16]([N:19]1[CH2:24][CH2:23][C:22](=O)[CH:21]([C:26](OC)=[O:27])[CH2:20]1)(=[O:18])[CH3:17].[O-]CC.[Na+].O>C(O)C>[OH:27][C:26]1[C:21]2[CH2:20][N:19]([C:16](=[O:18])[CH3:17])[CH2:24][CH2:23][C:22]=2[N:14]=[C:13]([NH:12][C:9]2[CH:8]=[CH:7][C:6]([C:5]3[O:1][CH:2]=[N:3][CH:4]=3)=[CH:11][CH:10]=2)[N:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 2723922Sodium ethoxideHCID 14143329Methyl 1-acetyl-4-oxopiperidine-3-carboxylateHCID 1785124711-(4-(Oxazol-5-yl)phenyl)guanidine

Product 1

HCID 1784737656-acetyl-2-[4-(1,3-oxazol-5-yl)anilino]-1,5,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-oneYield 61.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-(4-(Oxazol-5-yl)phenyl)guanidine (2.7 g, 13.35 mmol), methyl 1-acetyl-4-oxopiperidin-3-carboxylate (2.66 g, 13.35 mmol) and sodium ethoxide (0.946 g, 13.35 mmol) in ethanol (15 mL) were heated in a microwave reactor at 100° C. for 15 minutes. The reaction mixture was allowed to reach room temperature and water was added. The solid obtained was filtered, washed with water and dried in a vaccum oven yielding 1-(4-hydroxy-2-(4-(oxazol-5-yl)phenylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)ethanone (2.90 g, 61.8%).

Workup

  1. customto reach room temperature
  2. customThe solid obtained
  3. filtrationwas filtered
  4. washwashed with water
  5. customdried in a vaccum oven

Sources & evidence

ORD record
ord-b2fd778997304ac4ba4d10e05b8a7f0c
Source dataset
uspto-grants-2012_05
Patent number
US08188101B2

Reaction notes

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