Sodium Methoxide → 6-Benzyl-N-((6-methoxypyridin-3-yl)methyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-amine

HRID 657789Notes

Reaction equation

HRID 657789 reaction equation
[CH2:1]([N:8]1[CH2:26][CH2:25][C:11]2[N:12]=[CH:13][N:14]=[C:15]([NH:16][CH2:17][C:18]3[CH:19]=[N:20][C:21](Cl)=[CH:22][CH:23]=3)[C:10]=2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:27][O-:28].[Na+]>CO>[CH2:1]([N:8]1[CH2:26][CH2:25][C:11]2[N:12]=[CH:13][N:14]=[C:15]([NH:16][CH2:17][C:18]3[CH:19]=[N:20][C:21]([O:28][CH3:27])=[CH:22][CH:23]=3)[C:10]=2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 598407096-Benzyl-N-((6-chloropyridin-3-yl)methyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-amine

Product 1

HCID 598406976-Benzyl-N-((6-methoxypyridin-3-yl)methyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-amineYield 81.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A mixture of 6-benzyl-N-((6-chloropyridin-3-yl)methyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-amine (2.5 g, 6.8 mmol), MeOH (5 mL), and 15% wt. sodium methoxide solution (10 g, 48 mmol) in MeOH was subjected to microwave irradiation at 150° C. for 60 min. The mixture was concentrated in vacuo and the residue was treated with water (50 mL) and extracted with CH2Cl2 (3×50 mL). The combined organic layers were washed with brine, dried (Na2SO4), and concentrated. The residue was purified by silica gel column (MeOH/CH2Cl2: 0-15%) to yield a yellow solid (2.0 g, 79%).

Workup

  1. customirradiation at 150° C. for 60 min
  2. concentrationThe mixture was concentrated in vacuo
  3. additionthe residue was treated with water (50 mL)
  4. extractionextracted with CH2Cl2 (3×50 mL)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel column (MeOH/CH2Cl2: 0-15%)

Sources & evidence

ORD record
ord-4ee5dae3f4f34cacaa67ebfc6425da53
Source dataset
uspto-grants-2011_12
Patent number
US08076345B2

Reaction notes

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