Methanol → HCID 86666929, compound

HRID 511011Notes

Reaction equation

HRID 511011 reaction equation
[Cl:1][C:2]1[C:3]([CH3:31])=[C:4]([CH:28]2[CH2:30][O:29]2)[C:5]([O:26][CH3:27])=[C:6]([CH:8]([NH:10][C:11]2[N:19]=[CH:18][N:17]=[C:16]3[C:12]=2[N:13]=[CH:14][N:15]3[CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][O:21]2)[CH3:9])[CH:7]=1.[CH:32]([NH2:35])([CH3:34])[CH3:33].CCN(C(C)C)C(C)C.CO>C(Cl)Cl>[Cl:1][C:2]1[C:3]([CH3:31])=[C:4]([CH:28]([OH:29])[CH2:30][NH:35][CH:32]([CH3:34])[CH3:33])[C:5]([O:26][CH3:27])=[C:6]([CH:8]([NH:10][C:11]2[N:19]=[CH:18][N:17]=[C:16]3[C:12]=2[N:13]=[CH:14][N:15]3[CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][O:21]2)[CH3:9])[CH:7]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 6363IsopropylamineHCID 81531DiisopropylethylamineHCID 86666927HCID 86666927, compound

Product 1

HCID 86666929HCID 86666929, compoundYield 8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

N-[1-(5-chloro-2-methoxy-4-methyl-3-oxiran-2-ylphenyl)ethyl]-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine (140.0 mg, 0.32 mmol) was stirred in methylene chloride (1.1 mL). Isopropylamine (124 μL, 1.6 mmol) and DIPEA (282 pt, 1.62 mmol) were added. The mixture was stirred at 80° C. overnight. Methanol was added and purification by preparative LC/MS (pH 10) gave the desired compound (12.9 mg, 8%). LCMS calculated for C25H36ClN6O3 (M+H)+: m/z=503.3. found: 503.1.

Workup

  1. custompurification by preparative LC/MS (pH 10)

Sources & evidence

ORD record
ord-f0d3e3ed1a43414886950643ed45a152
Source dataset
uspto-grants-2015_08
Patent number
US09096600B2

Reaction notes

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