Methanol → HCID 178461672, compound

HRID 80800Notes

Reaction equation

HRID 80800 reaction equation
[NH2:1][C:2]([NH2:4])=[O:3].C[O-].[Na+].CO.O=[C:11]1[CH2:16][CH2:15][N:14]([C@H:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH3:18])[CH2:13][C@@H:12]1[C:25](OCC)=[O:26]>C1COCC1.O.CCOC(C)=O>[C:19]1([C@@H:17]([N:14]2[CH2:15][CH2:16][C:11]3[N:1]=[C:2]([OH:3])[N:4]=[C:25]([OH:26])[C:12]=3[CH2:13]2)[CH3:18])[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

8

Reactant 4

HCID 887MethanolHCID 1176UreaHCID 10942334Sodium MethoxideHCID 86690259HCID 86690259, compound

Product 1

HCID 178461672HCID 178461672, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A combination of urea (0.37 g, 15.6 mmol), sodium methoxide (1.47 g, 27.2 mmol) and MeOH (50 mL) was cooled to 0° C. and then a solution of (S)-ethyl 4-oxo-1-((S)-1-phenylethyl)piperidine-3-carboxylate (9.0 g, 7.8 mmol) in THF was added. The reaction mixture was allowed to warm to rt and then warmed to 60° C. and heated for 3 h. The mixture was diluted with water and EtOAc and the organic layer was then separated, dried (Na2SO4), filtered and concentrated. The residue was purified by FCC (8-10% MeOH/CH2Cl2) to give (S)-6-(1-phenylethyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine-2,4-diol.

Workup

  1. temperaturewarmed to 60° C.
  2. temperatureheated for 3 h
  3. customthe organic layer was then separated
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by FCC (8-10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-435961ec3ded4bf1a136b35e75fa1f25
Source dataset
uspto-grants-2014_09
Patent number
US08846656B2

Reaction notes

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