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

HRID 478615Notes

Reaction equation

HRID 478615 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 CH2Cl2, the organic layer washed with H2O, dried over MgSO4 and evaporated to give the subtitle compound as a brown oil (3.3 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 CH2Cl2
  5. washthe organic layer washed with H2O
  6. dry with materialdried over MgSO4
  7. customevaporated

Sources & evidence

ORD record
ord-ce8d10d2711649b8b01fd5249e26ac0c
Source dataset
uspto-grants-2003_11
Patent number
US06642242B2

Reaction notes

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