Triethylamine → N-(6-{[2-(acetylamino)ethyl]amino}-2-phenylpyrimidin-4-yl)-2-bromoacetamide
Reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:5]=[C:4]([NH:14][CH2:15][CH2:16][NH:17][C:18](=[O:20])[CH3:19])[CH:3]=1.C(N(CC)CC)C.[Br:28][CH2:29][C:30](Br)=[O:31]>ClCCl>[C:18]([NH:17][CH2:16][CH2:15][NH:14][C:4]1[N:5]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:7]=[C:2]([NH:1][C:30](=[O:31])[CH2:29][Br:28])[CH:3]=1)(=[O:20])[CH3:19]Participants
Procedure
To N-{2-[(6-amino-2-phenylpyrimidin-4-yl)amino]ethyl}acetamide (5) (1.20 g) in anhydrous dichloromethane (100 ml) was added triethylamine (1.23 ml), then bromoacetylbromide (768μl) in 2 aliquots. The mixture was left to stir at room temperature for 10 mins then was partitioned between dichloromethane (50 ml) and water (50 ml). The aqueous layer was extracted with dichloromethane (3×50 ml) and the organic layers combined, dried over magnesium sulfate and filtered. The solvent was removed in vacuo and the resulting solid purified via column chromatography on silica gel eluting with a mixture of ethyl acetate and petrol ether (1:1 v/v), then ethyl acetate, then a mixture of ethyl acetate and methanol (95:5 v/v) to furnish the title compound (195 mg).
Workup
- waitThe mixture was left
- customthen was partitioned between dichloromethane (50 ml) and water (50 ml)
- extractionThe aqueous layer was extracted with dichloromethane (3×50 ml)
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- customThe solvent was removed in vacuo
- customthe resulting solid purified via column chromatography on silica gel eluting with a mixture of ethyl acetate and petrol ether (1:1 v/v)
- additionethyl acetate, then a mixture of ethyl acetate and methanol (95:5 v/v)
Sources & evidence
- ORD record
- ord-b611b30c7c5242ae9229ea975121a05d
- Source dataset
- uspto-grants-2005_07
- Patent number
- US06916804B2
Reaction notes
Loading…