N-(2-aminoethyl)acetamide → N-{2-[(6-amino-2-phenylpyrimidin-4-yl)amino]ethyl}acetamide

HRID 895480

Reaction equation

Cl[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]([NH2:14])[CH:3]=1.[C:15]([NH:18][CH2:19][CH2:20][NH2:21])(=[O:17])[CH3:16]>CS(C)=O>[NH2:14][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:21][CH2:20][CH2:19][NH:18][C:15](=[O:17])[CH3:16])[CH:3]=1

Participants

Conditions

Temperature: 130 °C

Procedure

6-Chloro-2-phenylpyrimidin-4-amine (2.87 g) was dissolved in DMSO (50 ml) and N-acetylethylenediamine (14.28 g) added. The stirred solution was heated at 130° C. for 8 hrs then partitioned between ethyl acetate (500 ml) and saturated brine solution (400 ml). The organic phase was dried over magnesium sulfate, filtered and the solvent removed in vacuo. Purification by flash chromatography on silica gel eluting with first ethyl acetate then a mixture of ethyl acetate and methanol (9:1 then 8:2 v/v) yielded the title compound (2.50 g).

Workup

customthen partitioned between ethyl acetate (500 ml) and saturated brine solution (400 ml)
dry with materialThe organic phase was dried over magnesium sulfate
filtrationfiltered
customthe solvent removed in vacuo
customPurification by flash chromatography on silica gel eluting with first ethyl acetate
additiona mixture of ethyl acetate and methanol (9:1

Sources & evidence

ORD record: ord-ad91b898a2c341c0b67b41ee5ff2bf41
Source dataset: uspto-grants-2005_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06916804B2

Linked notes

Loading…