4,5-Dichloropyrimidin-2-amine → 5-chloro-N4-((2-(2-chlorophenyl)-8-methylquinolin-3-yl)methyl)pyrimidine-2,4-diamine

HRID 645929Notes

Reaction equation

HRID 645929 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:17]([CH2:18][NH2:19])=[CH:16][C:15]2[C:10](=[C:11]([CH3:20])[CH:12]=[CH:13][CH:14]=2)[N:9]=1.Cl[C:22]1[C:27]([Cl:28])=[CH:26][N:25]=[C:24]([NH2:29])[N:23]=1>C(O)CCCC>[Cl:28][C:27]1[C:22]([NH:19][CH2:18][C:17]2[C:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[Cl:1])=[N:9][C:10]3[C:15]([CH:16]=2)=[CH:14][CH:13]=[CH:12][C:11]=3[CH3:20])=[N:23][C:24]([NH2:29])=[N:25][CH:26]=1

Participants

4

Reactant 2

HCID 211860654,5-Dichloropyrimidin-2-amineHCID 59264626(2-(2-Chlorophenyl)-8-methylquinolin-3-yl)methanamine

Product 1

HCID 250700045-chloro-N4-((2-(2-chlorophenyl)-8-methylquinolin-3-yl)methyl)pyrimidine-2,4-diamine

Reagents, catalysts & solvents 1

HCID 62761-PentanolSolvent

Procedure

A mixture of (2-(2-chlorophenyl)-8-methylquinolin-3-yl)methanamine (0.050 g, 0.18 mmol), and 4,5-dichloro-2-aminopyrimidine (0.029 g, 0.18 mmol, 1 eq) were stirred in 1-pentanol (0.9 mL) at 80° C. for 4 days. After purification, 5-chloro-N4-((2-(2-chlorophenyl)-8-methylquinolin-3-yl)methyl)pyrimidine-2,4-diamine [PI3Kδ IC50=165 nM] was obtained as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.18 (1H, s), 7.86 (1H, d, J=7.8 Hz), 7.72 (1H, s), 7.45-7.64 (7H, m), 7.28 (1H, t, J=5.9 Hz), 6.02 (2H, s), 4.46 (2H, d, J=18.8 Hz), 2.65 (3H, s) Mass Spectrum (ESI) m/e=410.0 and 412.1 (M+1)

Workup

  1. customAfter purification

Sources & evidence

ORD record
ord-e1ee8058b0fe460f9676fbc27f5429e6
Source dataset
uspto-grants-2010_04
Patent number
US07705018B2

Reaction notes

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