2-Amino-4-chloro-6-phenylpyrimidine → N4-{2-[(2-aminopyrimidin-4-yl)amino]ethyl}-6-phenylpyrimidine-2,4-diamine

HRID 2386985Notes

Reaction equation

HRID 2386985 reaction equation
Cl.Cl.[NH2:3][CH2:4][CH2:5][NH:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([NH2:13])[N:8]=1.Cl[C:15]1[CH:20]=[C:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:18]=[C:17]([NH2:27])[N:16]=1>>[NH2:13][C:9]1[N:8]=[C:7]([NH:6][CH2:5][CH2:4][NH:3][C:15]2[CH:20]=[C:19]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[N:18]=[C:17]([NH2:27])[N:16]=2)[CH:12]=[CH:11][N:10]=1

Participants

3

Reactant 2

HCID 2408022-Amino-4-chloro-6-phenylpyrimidineHCID 86638141N4-(2-aminoethyl)pyrimidine-2,4-diamine dihydrochloride

Product 1

HCID 44609412N4-{2-[(2-aminopyrimidin-4-yl)amino]ethyl}-6-phenylpyrimidine-2,4-diamine

Procedure

The product of Example 1E (73 mg, 0.323 mmol) and 4-chloro-6-phenylpyrimidin-2-amine (51 mg, 0.248 mmol) were treated under the conditions of Example 1F to afford the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 7.84-7.93 (m, J=7.12, 2.37 Hz, 2H) 7.57-7.66 (m, 1H) 7.39-7.48 (m, 3H) 6.81-7.14 (m, 2H) 6.24 (s, 1H) 6.04 (s, 2H) 5.90 (s, 2H) 5.74 (d, J=5.76 Hz, 1H) 3.35-3.48 (m, 4H); MS (ESI+) m/z 323.0 (M+H)+.

Sources & evidence

ORD record
ord-f20c2e672d4f4d21be7cb12ea6020023
Source dataset
uspto-grants-2012_09
Patent number
US08268846B2

Reaction notes

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