Phosphorus oxychloride → 7-Benzyl-4-chloro-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine

HRID 1871492Notes

Reaction equation

HRID 1871492 reaction equation
[CH2:1]([N:8]1[CH2:17][C:16]2[N:15]=[CH:14][N:13]=[C:12](O)[C:11]=2[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O=P(Cl)(Cl)[Cl:21]>>[CH2:1]([N:8]1[CH2:17][C:16]2[N:15]=[CH:14][N:13]=[C:12]([Cl:21])[C:11]=2[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178517913HCID 178517913, compound

Product 1

HCID 219588387-Benzyl-4-chloro-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidineYield 81%

Conditions

Temperature
100 °C

Procedure

7-Benzyl-4-hydroxy-5,6,7,8-tetrahydro-1,3,7-triazanaphthalene [Ozdowska et al Rocz. Chem. Ann. Soc. Chim. Pol. 50,1771 (1976)] 95.0 g, 15.9 mmol) was added to POCl3 and the mixture heated to 100° C. for 1 h. The reaction was cooled, concentrated under reduced pressure and the residue quenched with ice. After neutralising with K2CO3 the product was extracted with CH2C2, the organic layer washed with H2O, dried over MgSO4 and evaporated to give the subtitle compound as a brown oil (3.33 g, 81%). Rf 0.45 (CH2Cl2 /MeOH/0.88NH3 92/7/1, v/v).

Workup

  1. temperatureThe reaction was cooled
  2. concentrationconcentrated under reduced pressure
  3. customthe residue quenched with ice
  4. extractionwas extracted with CH2C2
  5. washthe organic layer washed with H2O
  6. dry with materialdried over MgSO4
  7. customevaporated

Sources & evidence

ORD record
ord-ccae6e016239453caed89cfc5f960f98
Source dataset
uspto-grants-2000_08
Patent number
US06103738

Reaction notes

Loading…