4,6-Pyrimidinediamine, monohydrochloride → N4-((8-Chloro-2-(2-chlorophenyl)quinolin-3-yl)methyl)pyrimidine-4,6-diamine

HRID 2193520Notes

Reaction equation

HRID 2193520 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[Cl:18])[C:8]([CH2:19]Cl)=[CH:7]2.Cl.[NH2:22][C:23]1[CH:28]=[C:27]([NH2:29])[N:26]=[CH:25][N:24]=1.CCN(C(C)C)C(C)C>C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[Cl:18])[C:8]([CH2:19][NH:22][C:23]1[CH:28]=[C:27]([NH2:29])[N:26]=[CH:25][N:24]=1)=[CH:7]2

Participants

5

Reactant 3

HCID 796074,6-Pyrimidinediamine, monohydrochlorideHCID 81531DiisopropylethylamineHCID 592646338-Chloro-3-(chloromethyl)-2-(2-chlorophenyl)quinoline

Product 1

HCID 25070005N4-((8-Chloro-2-(2-chlorophenyl)quinolin-3-yl)methyl)pyrimidine-4,6-diamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Prepared according to Procedure H using 8-chloro-3-(chloromethyl)-2-(2-chlorophenyl)quinoline (0.035 g, 0.11 mmol), 4,6-diaminopyrimidine hydrochloride (0.032 g, 0.22 mmol, 2 eq) and DIEA (0.55 mL, 2.2 mmol, 20 eq) in ethanol (1 mL). N4-((8-Chloro-2-(2-chlorophenyl)quinolin-3-yl)methyl)pyrimidine-4,6-diamine [PI3Kδ IC50=6868 nM] was obtained after purification as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.32 (1H, s), 8.05 (1H, dd, J=8.4, 1.0 Hz), 7.95 (1H, dd, J=7.4, 1.2 Hz), 7.84 (1H, s), 7.51-7.67 (5H, m), 7.24 (1H, s), 6.19 (2H, s), 5.32 (1H, s), 4.33 (1H, s) Mass Spectrum (ESI) m/e=396.1 and 398.0 (M+1)

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-5a7ed12bb6034ac1b1254786be303551
Source dataset
uspto-grants-2012_12
Patent number
US08329910B2

Reaction notes

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