Reaction #85922

Reaction equation

water

(R)-tert-butyl 2-((7-(4-hydroxyphenyl)pyrido[4,3-b]pyrazin-5-ylamino)methyl)morpholine-4-carboxylate

Cs2CO3

3-bromopropan-1-ol

→

(R)-tert-butyl 2-((7-(4-(3-hydroxypropoxy)phenyl)pyrido[4,3-b]pyrazin-5-ylamino)methyl)morpholine-4-carboxylate

Solvents

DMF

Conditions

Workup

1. 1
   Extractionextracted with EA
2. 2
   Washwashed with water and brine
3. 3
   Otherdried
4. 4
   Concentrationconcentrated
5. 5
   Otherpurified on TLC (CH2Cl2:MeOH=30:1)
6. 6
   Otherto give yellow solid

Procedure

To a solution of (R)-tert-butyl 2-((7-(4-hydroxyphenyl)pyrido[4,3-b]pyrazin-5-ylamino)methyl)morpholine-4-carboxylate (115 mg, 0.26 mmol) in DMF (5 mL) was added Cs2CO3 (128 mg, 0.39 mmol) and 3-bromopropan-1-ol (55 mg, 0.39 mmol). The reaction was stirred at 80° C. for 0.5 hours. TLC and LC-Ms showed the reaction had completed and the reaction was poured into water, extracted with EA, washed with water and brine, dried and concentrated, purified on TLC (CH2Cl2:MeOH=30:1) to give yellow solid. MS (m/z): 496 (M+H)+

Source