Water → 2-benzyloxymethyl-3H-pyrido[2,3-d]pyrimidin-4-one

HRID 2100459Notes

Reaction equation

HRID 2100459 reaction equation
[CH2:1]([O:8][CH2:9][C:10]([NH:12][C:13]1[N:21]=[CH:20][CH:19]=[CH:18][C:14]=1[C:15]([NH2:17])=[O:16])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].O>O.CCO>[CH2:1]([O:8][CH2:9][C:10]1[NH:17][C:15](=[O:16])[C:14]2[CH:18]=[CH:19][CH:20]=[N:21][C:13]=2[N:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 10340Sodium CarbonateHCID 426324782-(2-Benzyloxy-acetylamino)-nicotinamide

Product 1

HCID 1358992352-benzyloxymethyl-3H-pyrido[2,3-d]pyrimidin-4-oneYield 21%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

2-(2-Benzyloxy-acetylamino)-nicotinamide (76 mg, 0.3 mmol) in H2O/EtOH (4 ml, 1:1) was stirred with sodium carbonate (28 mg, 0.3 mmol) at reflux for 2 hours. Water was added, the phases were separated and the inorganic layer was extracted with EtOAc (3 times). The combined organic layers were washed with brine, dried over Na2SO4, filtrated and concentrated in vacuo to yield 2-benzyloxymethyl-3H-pyrido[2,3-d]pyrimidin-4-one (15 mg, 21%) as a white solid, MS (m/e): 268.1 [M+].

Workup

  1. temperatureat reflux for 2 hours
  2. customthe phases were separated
  3. extractionthe inorganic layer was extracted with EtOAc (3 times)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltrated
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3e5b00ee475c4ba1acfb483cac2760f7
Source dataset
uspto-grants-2009_08
Patent number
US07572801B2

Reaction notes

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