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

HRID 657725Notes

Reaction equation

HRID 657725 reaction equation
[CH2:1]([N:8]1[CH2:18][CH2:17][C:11]2[N:12]=[CH:13][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.ClC1N=CC=CN=1.[CH3:26][O-:27].[Na+]>CO>[CH2:1]([N:8]1[CH2:18][CH2:17][C:11]2[N:12]=[CH:13][N:14]=[C:15]([O:27][CH3:26])[C:10]=2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 744042-ChloropyrimidineHCID 10942334Sodium MethoxideHCID 253240466-Benzyl-4-chloro-5,6,7,8-tetrahydropyrido(4,3-d)pyrimidine

Product 1

HCID 581035816-Benzyl-4-methoxy-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidineYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A 1 L flask was charged with 6-benzyl-4-chloro-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine (39.6 g, 0.152 mol) and methanol (300 mL), and the mixture was heated to dissolve the chloropyrimidine. 4.37 M of sodium methoxide in methanol (105 mL) was added slowly to the warm mixture and the stirred mixture rapidly turned cloudy. The resultant suspension was heated under reflux for 2 h. After cooling, the mixture was concentrated in vacuo to ca 100 mL. The residue was poured into water (600 mL), and extracted with CH2Cl2 (200 mL×2). The combined organic layers were washed with brine (400 mL), dried (Na2SO4), filtered and concentrated in vacuo to yield a light brown oil (38.9 g, 100%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 h
  3. temperatureAfter cooling
  4. concentrationthe mixture was concentrated in vacuo to ca 100 mL
  5. additionThe residue was poured into water (600 mL)
  6. extractionextracted with CH2Cl2 (200 mL×2)
  7. washThe combined organic layers were washed with brine (400 mL)
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b5967560d4704e20b5ff42c84cfb933c
Source dataset
uspto-grants-2011_12
Patent number
US08076345B2

Reaction notes

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