Acetic Acid → HCID 178494209, compound

HRID 242322Notes

Reaction equation

HRID 242322 reaction equation
CO[C:3]([CH:5]1[C:10](=O)[CH2:9][CH2:8][N:7]([C:12]2[CH:13]=[N:14][C:15]([O:19][CH3:20])=[C:16]([CH3:18])[CH:17]=2)[CH2:6]1)=[O:4].C(O)(=O)C.[CH:25]([NH2:27])=[NH:26].C[O-].[Na+].C(O)(=O)C>CO.C(Cl)Cl>[CH3:20][O:19][C:15]1[N:14]=[CH:13][C:12]([N:7]2[CH2:8][CH2:9][C:10]3[N:26]=[CH:25][N:27]=[C:3]([OH:4])[C:5]=3[CH2:6]2)=[CH:17][C:16]=1[CH3:18]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 160693Formamidine acetateHCID 10942334Sodium MethoxideHCID 66653516HCID 66653516, compound

Product 1

HCID 178494209HCID 178494209, compoundYield 76.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 6′-methoxy-5′-methyl-4-oxo-3,4,5,6-tetrahydro-2H-[1,3]bipyridinyl-3-carboxylic acid methyl ester (900 mg, 3.23 mmol), formamidine acetate (521 mg, 4.85 mmol), sodium methoxide (5.4 Molar) in methanol (2.395 mL, 12.94 mmol) and methanol (4 mL) was heated to 90° C. for 3 h. The mixture was allowed to cool down to rt, diluted in CH2Cl2, neutralized with acetic acid (0.741 mL, 12.94 mmol) and quenched with H2O. The layers were separated and aqueous was washed twice with CH2Cl2, organics were combined, washed with brine, dried over sodium sulfate, filtered and evaporated to give a yellow solid. The solid was triturated in ethylacetate to yield 6-(6-methoxy-5-methyl-pyridin-3-yl)-5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidin-4-ol (669 mg, yield 76%) as a white powder. 1H-NMR (400 MHz, DMSO-d6, 298K) δ ppm 2.14 (s, 3H) 2.72 (t, 2H) 3.39 (t, 2H) 3.81 (s, 3H) 3.90 (s, 2H) 7.42 (d, 1H) 7.67 (d, 1H) 8.07 (s, 1H) 12.46 (br.s., 1H). LCMS: [M+H]+=273.1, Rt(3)=1.30 min.

Workup

  1. temperatureto cool down to rt
  2. customquenched with H2O
  3. customThe layers were separated
  4. washaqueous was washed twice with CH2Cl2
  5. washwashed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customto give a yellow solid
  10. customThe solid was triturated in ethylacetate

Sources & evidence

ORD record
ord-3fd7b172f7de4fda9279a2d446981aab
Source dataset
uspto-grants-2014_02
Patent number
US08653092B2

Reaction notes

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