Sodium Methoxide → 6-Benzyl-2-chloro-4-methoxy-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine

HRID 80762Notes

Reaction equation

HRID 80762 reaction equation
[CH2:1]([N:8]1[CH2:19][CH2:18][C:11]2[N:12]=[C:13]([Cl:17])[N:14]=[C:15](Cl)[C:10]=2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:20][O-:21].[Na+]>CO>[CH2:1]([N:8]1[CH2:19][CH2:18][C:11]2[N:12]=[C:13]([Cl:17])[N:14]=[C:15]([O:21][CH3:20])[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 378190156-Benzyl-2,4-dichloro-5,6,7,8-tetrahydropyrido(4,3-d)pyrimidine

Product 1

HCID 866902516-Benzyl-2-chloro-4-methoxy-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 6-benzyl-2,4-dichloro-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine (6.38 g, 21.69 mmol) in anhydrous methanol (100 mL), was added 4.67 N sodium methoxide (5.57 mL, 26 mmol) slowly at 0° C. The reaction mixture was stirred at 0° C. for 15 min, then at rt for 30 min. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in DCM and washed with brine, dried over Na2SO4, filtered, and concentrated to give 6-benzyl-2-chloro-4-methoxy-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine which was used without the need for purification. 1H NMR (400 MHz, CD2Cl2) δ ppm 7.31-7.40 (m, 4 H), 7.23-7.31 (m, 1 H), 3.95 (s, 3 H), 3.72 (br. s., 2 H), 3.43 (br. s., 2 H), 2.84 (d, J=4.5 Hz, 2 H), 2.78 (d, J=4.0 Hz, 2 H). MS (ESI+) m/z 290.4 (M+H)+.

Workup

  1. waitat rt for 30 min
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in DCM
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c371a54e707449aa8e132a03ad5a3e5a
Source dataset
uspto-grants-2014_09
Patent number
US08846656B2

Reaction notes

Loading…