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

HRID 2183698Notes

Reaction equation

HRID 2183698 reaction equation
[CH2:1]([N:8]1[CH2:17][CH2:16][C:15]2[C:14](=O)[NH:13][CH:12]=[N:11][C:10]=2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)C1C=CC=CC=1)C.O=P(Cl)(Cl)[Cl:32]>>[CH2:1]([N:8]1[CH2:17][CH2:16][C:15]2[C:14]([Cl:32])=[N:13][CH:12]=[N:11][C:10]=2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 7061N,N-DiethylanilineHCID 24813Phosphorus oxychlorideHCID 1357235075,6,7,8-Tetrahydro-7-(phenylmethyl)pyrido(3,4-d)pyrimidin-4(3H)-one

Product 1

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

Conditions

Temperature
80 °C

Procedure

To a mixture of 7-benzyl-5,6,7,8-tetrahydro-3H-pyrido[3,4-d]pyrimidin-4-one 3a (1.0 g, 4.14 mmol) and N,N-diethylaniline (0.37 g, 2.48 mmol) was slowly added POCl3 (12 mL). The mixture was heated to 80° C. for 20 h. After evaporation of the excess of POCl3, the residue was poured into ice, dichloromethane was added and the mixture was made basic (pH=11) with solid Na2CO3. The product was extracted with dichloromethane, dried, and concentrated. Flash column chromatography with 20% ethyl acetate:hexane gave 0.46 g of 7-benzyl-4-chloro-5,6,7,8-tetrahydro-pyrido[3,4-d]pyrimidine 4a as a yellow oil.

Workup

  1. customAfter evaporation of the excess of POCl3
  2. additionthe residue was poured into ice, dichloromethane
  3. additionwas added
  4. extractionThe product was extracted with dichloromethane
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1748ba6f80fb45b083d275b0c1c08bb6
Source dataset
uspto-grants-2005_05
Patent number
US06900220B2

Reaction notes

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