Water → 4-(7-bromo-3-methyl-3,4-dihydroisoquinolin-2(1H)-yl)-6-(4-methylpiperazin-1-yl)pyrimidin-2-amine

HRID 2090344Notes

Reaction equation

[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH:7]([CH3:20])[N:8]([C:12]3[CH:17]=[C:16](Cl)[N:15]=[C:14]([NH2:19])[N:13]=3)[CH2:9]2)=[CH:4][CH:3]=1.[CH3:21][N:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1.O>C(O)(C)(C)C>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH:7]([CH3:20])[N:8]([C:12]3[CH:17]=[C:16]([N:25]4[CH2:26][CH2:27][N:22]([CH3:21])[CH2:23][CH2:24]4)[N:15]=[C:14]([NH2:19])[N:13]=3)[CH2:9]2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 4-(7-bromo-3-methyl-3,4-dihydroisoquinolin-2(1H)-yl)-6-chloropyrimidin-2-amine (2.3 g, 6.5 mmol) and 1-methyl piperazine (3.61 mL, 32.6 mmol) in tert-butyl alcohol (10 mL) and was heated at 120° C. for 20 h. The reaction mixture was cooled to r.t., poured into water, extracted with AcOEt, washed with sat'd NaHCO3 aqueous solution and brine, dried with MgSO4. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column using 10% methanol in methylene chloride to afford the desired compound. LCMS (M+H)+: m/z=417.1.

Workup

temperatureThe reaction mixture was cooled to r.t.
extractionextracted with AcOEt
washwashed with sat'd NaHCO3 aqueous solution and brine
dry with materialdried with MgSO4
filtrationAfter filtration
concentrationthe filtrate was concentrated under reduced pressure
customThe residue was purified by flash chromatography on a silica gel column

Sources & evidence

ORD record: ord-bbd18f0ab44e4b29b97f358831e492ff
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08436008B2

Reaction notes

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