Triethylamine → HCID 46701253, compound

HRID 2090298Notes

Reaction equation

Cl[C:2]1[CH:7]=[C:6]([N:8]2[CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH2:9]2)[N:5]=[C:4]([NH2:15])[N:3]=1.[CH2:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:19][C@@H:18]([CH2:26][OH:27])[NH:17]1.C(N(CC)CC)C>CN1CCCC1=O.CO>[NH2:15][C:4]1[N:3]=[C:2]([N:17]2[C@H:18]([CH2:26][OH:27])[CH2:19][C:20]3[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:16]2)[CH:7]=[C:6]([N:8]2[CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH2:9]2)[N:5]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 4-chloro-6-(4-methylpiperazin-1-yl)pyrimidin-2-amine (20 mg, 87.8 mmol), (3 S)-1,2,3,4-tetrahydroisoquinolin-3-ylmethanol (21.5 mg, 132 mmol, Aldrich, Cat. 494186) and triethylamine (0.5 mL, 4 mmol) in N-methylpyrrolidinone (1 mL) was heated at 120° C. overnight. The reaction mixture was diluted in MeOH, and purified by RP-HPLC (pH=10) to afford the desired compound. LCMS (M+H)+: m/z=355.3.

Workup

custompurified by RP-HPLC (pH=10)

Sources & evidence

ORD record: ord-8904c5c4867644418f42fe07594f247a
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08436008B2

Reaction notes

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