4-Methylpiperazine-1-ethylamine → N4-(5-Isopropyl-1H-pyrazol-3-yl)-N6-[2-(4-methylpiperazin-1-yl)ethyl]-N2-(3-phenylisoxazol-5-ylmethyl)-pyrimidine-2,4,6-triamine

HRID 1510401Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([NH:8][CH2:9][C:10]2[O:14][N:13]=[C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:11]=2)[N:5]=[C:4]([NH:21][C:22]2[CH:26]=[C:25]([CH:27]([CH3:29])[CH3:28])[NH:24][N:23]=2)[CH:3]=1.[CH3:30][N:31]1[CH2:36][CH2:35][N:34]([CH2:37][CH2:38][NH2:39])[CH2:33][CH2:32]1>C(O)CCC.CO>[CH:27]([C:25]1[NH:24][N:23]=[C:22]([NH:21][C:4]2[CH:3]=[C:2]([NH:39][CH2:38][CH2:37][N:34]3[CH2:35][CH2:36][N:31]([CH3:30])[CH2:32][CH2:33]3)[N:7]=[C:6]([NH:8][CH2:9][C:10]3[O:14][N:13]=[C:12]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)[CH:11]=3)[N:5]=2)[CH:26]=1)([CH3:29])[CH3:28]

Participants

Conditions

Temperature: 180 °C

Procedure

A mixture of 6-chloro-N4-(5-isopropyl-1H-pyrazol-3-yl)-N2-(3-phenylisoxazol-5-ylmethyl)-pyrimidine-2,4-diamine (250 mg, 0.611 mmol) and 2-(4-methylpiperazin-1-yl)-ethylamine (500 mg, 3.50 mmol) in 1-butanol (2 mL) was heated to 180° C. in a 50 mL sealed tube. The mixture was heated for 1 h, then cooled to room temperature and diluted with methanol (10 mL). The mixture thus obtained was purified via preparative reverse phase HPLC to give the desired product (93 mg, 29%) as a white solid.

Workup

customsealed tube
temperatureThe mixture was heated for 1 h
temperaturecooled to room temperature
customThe mixture thus obtained
customwas purified via preparative reverse phase HPLC

Sources & evidence

ORD record: ord-eed471f86ec54a9f80720b4678618e8b
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08211929B2

Reaction notes

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