反応 #88440

反応方程式

4-chlorobenzaldehyde

3-(3-(tert-butyldimethylsilyloxy)propyl)-6-chloro-1-methylpyrido[3,4-d]pyrimidine-2,4(1H,3H)-dione

LDA

→

3-(3-(tert-butyldimethylsilyloxy)propyl)-6-chloro-5-((4-chlorophenyl)(hydroxy)methyl)-1-methylpyrido[3,4-d]pyrimidine-2,4(1H,3H)-dione

収率 30.0%

溶媒

THF

THF

反応条件

後処理

1. 1
   workup.STIRRINGAfter stirring for 20 min the reaction
2. 2
   その他was quenched with aq. NH4Cl (2 mL)
3. 3
   workup.ADDITIONthen diluted with EA (5 mL) and water (2 mL)
4. 4
   洗浄The organic layer was washed with brine (5 mL)
5. 5
   乾燥dried over Na2SO4
6. 6
   濃縮concentrated to a residue which
7. 7
   その他was purified by chromatography
8. 8
   洗浄eluted with PE/EA (2:1)

実験手順

To a solution of 3-(3-(tert-butyldimethylsilyloxy)propyl)-6-chloro-1-methylpyrido[3,4-d]pyrimidine-2,4(1H,3H)-dione (383 mg, 1 mmol) in THF (4 mL) at −78° C. was added LDA (1.8N in THF, 2.7 mL, 4.86 mmol) dropwise. The reaction was stirred at −78° C. for 30 min then 4-chlorobenzaldehyde (280 mg, 2 mmol) in THF (1 mL) was added dropwise. After stirring for 20 min the reaction was quenched with aq. NH4Cl (2 mL) then diluted with EA (5 mL) and water (2 mL). The organic layer was washed with brine (5 mL), dried over Na2SO4 and concentrated to a residue which was purified by chromatography eluted with PE/EA (2:1) to give 3-(3-(tert-butyldimethylsilyloxy)propyl)-6-chloro-5-((4-chlorophenyl)(hydroxy)methyl)-1-methylpyrido[3,4-d]pyrimidine-2,4(1H,3H)-dione (155 mg, 30% yield) as a white solid. LCMS: (M+-OH—H) 506 and TR=2.357 min.

出典