Carbonic acid-guanidine (1:1) → 6-{2-[(4-Methoxybenzyl)oxy]pyridin-3-yl}-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine

HRID 632825Notes

Reaction equation

HRID 632825 reaction equation
CN([CH:4]=[C:5]1[C:10](=O)[CH2:9][CH2:8][N:7]([C:12]2[C:13]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=3)=[N:14][CH:15]=[CH:16][CH:17]=2)[CH2:6]1)C.C(=O)(O)O.[NH2:32][C:33]([NH2:35])=[NH:34].O.O.O.C([O-])(=O)C.[Na+]>C(O)C>[CH3:27][O:26][C:23]1[CH:22]=[CH:21][C:20]([CH2:19][O:18][C:13]2[C:12]([N:7]3[CH2:8][CH2:9][C:10]4[N:34]=[C:33]([NH2:35])[N:32]=[CH:4][C:5]=4[CH2:6]3)=[CH:17][CH:16]=[CH:15][N:14]=2)=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 286947Carbonic acid-guanidine (1:1)HCID 23665404Sodium Acetate TrihydrateHCID 1212495823-Dimethylaminomethylene-2'-(4-methoxybenzyloxy)-2,3,5,6-tetrahydro[1,3']bipyridinyl-4-one

Product 1

HCID 1212495836-{2-[(4-Methoxybenzyl)oxy]pyridin-3-yl}-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3-dimethylaminomethylene-2′-(4-methoxybenzyloxy)-2,3,5,6-tetrahydro[1,3′]bipyridinyl-4-one (673 mg, 1.83 mmol) in ethanol (100 ml) was treated with guanidine carbonate (1.32 g, 7.33 mmol), followed by addition of sodium acetate trihydrate (1.99 g, 14.64 mmol) and the reaction mixture was refluxed for 21 hours. The solvent was removed in vacuo and the residue was partitioned between water and ethyl acetate. The separated organic layer was dried (MgSO4), filtered, and concentrated. Elution through a flash column (silica gel 60, 230-400 mesh, 6% methanol in EtOAc) gave the title compound as a light yellow, amorphous solid (477 mg, 72%).

Workup

  1. temperaturethe reaction mixture was refluxed for 21 hours
  2. customThe solvent was removed in vacuo
  3. customthe residue was partitioned between water and ethyl acetate
  4. dry with materialThe separated organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. washElution through a flash column (silica gel 60, 230-400 mesh, 6% methanol in EtOAc)

Sources & evidence

ORD record
ord-1923efe991244fc4821d0d3486214983
Source dataset
uspto-grants-2016_04
Patent number
US09321766B1

Reaction notes

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