4-Ethoxyaniline → N2-(4-Ethoxyphenyl)-5-methoxycarbonyl-4-trifluoromethyl-2-pyrimidineamine

HRID 71291

Reaction equation

HRID 71291 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[C:5]([C:12]([O:14][CH3:15])=[O:13])=[CH:4][N:3]=1.[CH2:16]([O:18][C:19]1[CH:25]=[CH:24][C:22]([NH2:23])=[CH:21][CH:20]=1)[CH3:17].C(OC1C=CC=CC=1NC1N=C(C(F)(F)F)C(C(OC)=O)=CN=1)C>>[CH2:16]([O:18][C:19]1[CH:25]=[CH:24][C:22]([NH:23][C:2]2[N:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[C:5]([C:12]([O:14][CH3:15])=[O:13])=[CH:4][N:3]=2)=[CH:21][CH:20]=1)[CH3:17]

Participants

4

Reactant 3

HCID 90764-EthoxyanilineHCID 3696469Methyl 2-chloro-4-(trifluoromethyl)pyrimidine-5-carboxylateHCID 22060734N2-(2-ethoxyphenyl)-5-methoxycarbonyl-4-trifluoromethyl-2-pyrimidineamine

Product 1

HCID 22060255N2-(4-Ethoxyphenyl)-5-methoxycarbonyl-4-trifluoromethyl-2-pyrimidineamine

Procedure

In like manner to the preparation of N-(2-chloro-5-ethoxycarbonyl-4-pyrimidinyl)-L-phenylalanine Ethyl Ester, 2-chloro-5-methoxycarbonyl-4-trifluoromethylpyrimidine and 4-ethoxyaniline were reacted to prepare N2-(2-ethoxyphenyl)-5-methoxycarbonyl-4-trifluoromethyl-2-pyrimidineamine. 1H NMR (CDCl3): δ 8.98 (s, 1H), 7.47 (m, 3H), 6.91 (dd, 2H, J=2.1 and 6.9 Hz), 4.05 (q, 2H, 6.9 Hz), 1.42 (t, 3H, J=6.8 Hz); 19F NMR (CDCl3): −19105; LCMS: ret. time: 33.87 min; purity: 100%; MS (m/e): 342 (MH+).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-16c1437f579643ba90770e9ae5de0aa1
Source dataset
uspto-grants-2014_09
Patent number
US08822685B2

Linked notes

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