تفاعل #76129

معادلة التفاعل

2-acetoxymethyl-7-chloro-6-methyl-3,4-dihydroquinazolin-4-one

sodium hydride

iodomethane

→

solid

المردود 67.0%

2-Acetoxymethyl-7-chloro-3,6-dimethyl-3,4-dihydroquinazolin-4-one

المردود 67.0%

المذيبات

DMF

dichloromethane

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGStirring
2. 2
   workup.WAITwas continued at room temperature for 1 hour
3. 3
   أخرىthe reaction mixture was then partitioned between ethyl acetate (130 ml) and brine (80 ml)
4. 4
   غسيلThe organic layer was washed with dilute brine (80 ml)
5. 5
   تجفيفdried (Na2SO4)
6. 6
   تركيزconcentrated in vacuo
7. 7
   أخرىto leave an orange residue
8. 8
   workup.ADDITIONwas added
9. 9
   أخرىThe solvent was removed in vacuo
10. 10
    غسيلThe column was eluted with 5% ethyl acetate in dichloromethane

الإجراء التجريبي

To a suspension of 2-acetoxymethyl-7-chloro-6-methyl-3,4-dihydroquinazolin-4-one 0.428 g, 1.6 mmol) in anhydrous DMF (13 ml) was added sodium hydride (60% dispersion, 0.070 g, 1.76 mmol) under argon. Stirring was continued at room temperature for 1 min and then iodomethane (0.20 ml, 3.2 mmol) was added into the reaction mixture with a syringe via a septum. Stirring was continued at room temperature for 1 hour and the reaction mixture was then partitioned between ethyl acetate (130 ml) and brine (80 ml). The organic layer was washed with dilute brine (80 ml), dried (Na2SO4) and concentrated in vacuo to leave an orange residue. This orange residue was dissolved in dichloromethane and to this solution silica gel (Art 7734, 1.7 g) was added. The solvent was removed in vacuo and the orange free running powder was placed on a silica gel column made up in 5% ethyl acetate in dichloromethane. The column was eluted with 5% ethyl acetate in dichloromethane to afford a pale yellow solid (0.300 g, 67%), mp 110-112° C.; 1H-NMR (DMSO-d6) 2.17 (s, 3H, CH3CO), 2.47 (s, 3H, 6-CH3), 3.54 (s, 3H, N3—CH3), 5.23 (s, 2H, 2-CH2O), 7.71, 8.09 (2×s, 2H, 5-H, 8-H).

المصدر