p-Aminophenylacetic acid ethyl ester → N2,N4-bis[4-(ethoxycarbonylmethyl)phenyl]-5-cyano-2,4-pyrimidinediamine

반응식

O[C:2]1[CH:3]=[C:4]([NH:8][C:9]2[N:14]=[C:13]([NH:15][C:16]3[CH:21]=[CH:20][CH:19]=[C:18](O)[CH:17]=3)[C:12](F)=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1.ClC1N=C(Cl)C([C:32]#[N:33])=CN=1.NC1C=CC([CH2:41][C:42]([O:44][CH2:45][CH3:46])=[O:43])=CC=1>>[CH2:45]([O:44][C:42]([CH2:41][C:7]1[CH:6]=[CH:5][C:4]([NH:8][C:9]2[N:14]=[C:13]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([CH2:41][C:42]([O:44][CH2:45][CH3:46])=[O:43])=[CH:18][CH:17]=3)[C:12]([C:32]#[N:33])=[CH:11][N:10]=2)=[CH:3][CH:2]=1)=[O:43])[CH3:46]

참가 물질

반응물 3

HCID 225219p-Aminophenylacetic acid ethyl ester

HCID 9904854R-112

HCID 140269072,4-Dichloro-5-cyanopyrimidine

생성물 1

HCID 22060613N2,N4-bis[4-(ethoxycarbonylmethyl)phenyl]-5-cyano-2,4-pyrimidinediamine

실험 절차

In a manner similar to the preparation of N2,N4-bis(3-hydroxyphenyl)-5-fluoro-2,4-pyrimidinediamine, 2,4-dichloro-5-cyanopyrimidine and ethyl 4-aminophenylacetate were reacted to yield N2,N4-bis[4-(ethoxycarbonylmethyl)phenyl]-5-cyano-2,4-pyrimidinediamine. 1H NMR (CDCl3): δ 8.29 (bs, 1H), 7.46 (2d, 4H, J=7.8 Hz), 7.28 (d, 2 h, J=8.1 Hz), 7.19 (d, 2H, J=8.1 Hz), 4.16 (2q, 4H, J=6.3 Hz), 3.64 (s, 2H), 3.59 (s, 2H), 1.30-1.23 (m, 6H); LCMS: ret. time: 29.29 min.; purity: 93%; MS (m/e): 461 (MH+).