Diisopropylethylamine → N-(2-(4-ethylpiperazin-1-yl)ethyl)-5-phenyl-6-(4-(2-(pyrrolidin-1-yl)ethoxy)phenyl)furo[2,3-d]pyrimidin-4-amine

HRID 502641Notes

Reaction equation

HRID 502641 reaction equation
Cl[C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[C:9]([C:17]3[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][N:26]4[CH2:30][CH2:29][CH2:28][CH2:27]4)=[CH:19][CH:18]=3)[O:8][C:4]=2[N:5]=[CH:6][N:7]=1.[CH2:31]([N:33]1[CH2:38][CH2:37][N:36]([CH2:39][CH2:40][NH2:41])[CH2:35][CH2:34]1)[CH3:32].CCN(C(C)C)C(C)C>C(Cl)Cl.CC#N>[CH2:31]([N:33]1[CH2:38][CH2:37][N:36]([CH2:39][CH2:40][NH:41][C:2]2[C:3]3[C:10]([C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=4)=[C:9]([C:17]4[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][N:26]5[CH2:30][CH2:29][CH2:28][CH2:27]5)=[CH:19][CH:18]=4)[O:8][C:4]=3[N:5]=[CH:6][N:7]=2)[CH2:35][CH2:34]1)[CH3:32]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 7766222-(4-Ethylpiperazin-1-yl)ethan-1-amineHCID 586032684-Chloro-5-phenyl-6-(4-(2-(pyrrolidin-1-yl)ethoxy)phenyl)furo[2,3-d]pyrimidine

Product 1

HCID 11663866N-(2-(4-ethylpiperazin-1-yl)ethyl)-5-phenyl-6-(4-(2-(pyrrolidin-1-yl)ethoxy)phenyl)furo[2,3-d]pyrimidin-4-amine

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 27 (60 mg, 0.143 mmol), 2-(4-ethylpiperazin-1-yl)ethanamine (57 mg, 0.362 mmol), and DIEA (0.062 mL, 0.357 mmol) in CH2Cl2 (1 mL) and CH3CN (1 mL) was heated at 70° C. over night, then concentrated. Preparative TLC (SiO2, 20% MeOH in CH2Cl2) afforded the title compound 28. MS for C32H40N6O2: found 541 (M+H+), 539 (M−H+).

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-ae243062014e463eba71bac8da037e7e
Source dataset
uspto-grants-2010_08
Patent number
US07776867B2

Reaction notes

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