7-BENZYL-4-CHLORO-2-METHYL-5,6,7,8-TETRAHYDROPYRIDO[3,4-D]PYRIMIDINE synthesis
- Product Name:7-BENZYL-4-CHLORO-2-METHYL-5,6,7,8-TETRAHYDROPYRIDO[3,4-D]PYRIMIDINE
- CAS Number:300552-41-4
- Molecular formula:C15H16ClN3
- Molecular Weight:273.76
![7-Benzyl-2-Methyl-5,6,7,8-tetrahydro-3H-pyrido[3,4-d]pyriMidin-4-one](/CAS/20150408/GIF/62259-92-1.gif)
62259-92-1
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300552-41-4
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Yield:300552-41-4 96%
Reaction Conditions:
with N-ethyl-N,N-diisopropylamine;trichlorophosphate in toluene at 25; for 2 h;Reflux;Inert atmosphere;
Steps:
Part B: Preparation of 7-benzyl-4-chloro-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine (49)
General procedure: To a mixture of 7-benzyl-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4(3H)-one4.83 g, 20.0 mmol) in toluene (80 mL) at 25 °C was added N,N-diisopropylethylamine (3.4 5 8 mL, 20.0 mmol), followed by phosphorous oxychloride (2.24 mL, 24.0 mmol). The reaction mixture was heatedat reflux for 2 h. After cooling to room temperature, the mixture was diluted with water and ethyl acetate. The aqueous phase was adjusted to ~pH 7 employing saturated aqueous sodium bicarbonate solution. The phases were separated. The organic phase was washed with water and brine, dried over anhyd. sodium sulfate, filtered and concentrated. The residue was dissolved in 1-chlorobutane, and the resulting mixture was filtered. The filtrate was concentrated under vacuum to provide 7-benzyl-4-chloro-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine (4.75 g, 91%) as an orange-red oil; LC/MS: m/z 260.10 (M + H)+, 0.948min (method 12).
References:
Swidorski, Jacob J.;Liu, Zheng;Yin, Zhiwei;Wang, Tao;Carini, David J.;Rahematpura, Sandhya;Zheng, Ming;Johnson, Kim;Zhang, Sharon;Lin, Pin-Fang;Parker, Dawn D.;Li, Wenying;Meanwell, Nicholas A.;Hamann, Lawrence G.;Regueiro-Ren, Alicia [Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,# 1,p. 160 - 167] Location in patent:supporting information
![Pyrido[3,4-d]pyrimidin-4(4aH)-one, 5,6,7,8-tetrahydro-2-methyl-7-(phenylmethyl)-](/CAS/20180702/GIF/745066-54-0.gif)
745066-54-0
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300552-41-4
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52763-21-0
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$6.00/1g
300552-41-4
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