p-Toluidine → HCID 10226138, compound

HRID 2375473Notes

Reaction equation

Cl[C:2]1[CH:7]=[C:6]([N:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[N:5]=[C:4]([N:14]([CH2:26][CH3:27])[CH2:15][CH2:16][C:17]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[NH:19][CH:18]=2)[N:3]=1.[NH2:28][C:29]1[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][CH:30]=1>>[CH2:26]([N:14]([CH2:15][CH2:16][C:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[NH:19][CH:18]=1)[C:4]1[N:3]=[C:2]([NH:28][C:29]2[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][CH:30]=2)[CH:7]=[C:6]([N:8]2[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]2)[N:5]=1)[CH3:27]

Participants

Reactant 2

HCID 7813p-Toluidine

HCID 21101363HCID 21101363, compound

Product 1

HCID 10226138HCID 10226138, compound

Conditions

Temperature: 160 °C

Procedure

A mixture of N-[4-chloro-6-(1-piperidinyl)-2-pyrimidinyl]-N-ethyl-N-[2-(1H-indol-3-yl)ethyl]amine (33.4 mg, 0.087 mmol) and p-toluidine (47 mg, 0.43 mmol) was heated neat under argon at 160° C. in a sealed tube for 12 hours. The crude material was purified by preparative TLC, eluting with hexane/ethyl acetate (4:1). N2-Ethyl-N2-[2-(1H-3-indolyl)ethyl]-N4-(4-methylphenyl)-6-piperidino-2,4-pyrimidinediamine was obtained, from a band at Rf=0.37, as a solid (15 mg, 0.033 mmol, 38%).

Workup

customThe crude material was purified by preparative TLC
washeluting with hexane/ethyl acetate (4:1)

Sources & evidence

ORD record: ord-b3fda611c4b3442a8574f767c840df63
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07465750B2

Reaction notes

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