Diisopropylethylamine → N-[1-(3-bromo-5-chloro-2-methoxy-4-methylphenyl)ethyl]-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine

HRID 510900Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 1-(3-bromo-5-chloro-2-methoxy-4-methylphenyl)ethanamine (5.0 g, 18 mmol), 6-bromo-9-(tetrahydro-2H-pyran-2-yl)-9H-purine (7.0 g, 25 mmol) and N,N-diisopropylethylamine (9.4 mL, 54 mmol) in ethanol (100 mL) was heated at 100° C. (flushed with nitrogen) overnight. The reaction mixture was cooled, poured into saturated sodium bicarbonate solution and extracted with ethyl acetate. The combined organic layers were washed with water and brine, dried over MgSO4, filtered and concentrated. The residue was purified on silica gel (eluting with 0-65% ethyl acetate in hexane) to afford the desired product. LCMS calculated for C20H24BrClN5O2 (M+H)+: m/z=480.1, 4821. found: 480.0, 482.1.

Workup

custom(flushed with nitrogen) overnight
temperatureThe reaction mixture was cooled
additionpoured into saturated sodium bicarbonate solution
extractionextracted with ethyl acetate
washThe combined organic layers were washed with water and brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated
customThe residue was purified on silica gel (eluting with 0-65% ethyl acetate in hexane)

Sources & evidence

ORD record: ord-5724d0f89b5d4899a4d84a08247d7a22
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096600B2

Reaction notes

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