2-Chloropyrimidine → HCID 86583555, compound

HRID 1790578Notes

Reaction equation

HRID 1790578 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]#[N:23])=[CH:18][CH:17]=2)[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:5]=[C:6]([CH3:8])[CH:7]=1.Cl[C:25]1[N:30]=[CH:29][CH:28]=[CH:27][N:26]=1.C(N(C(C)C)CC)(C)C.[N:40]12[CH2:50][CH2:49][CH2:48][N:47]=[C:46]1[CH2:45][CH2:44][CH2:43][CH2:42][CH2:41]2>C1COCC1>[C:22]([C:19]1[CH:18]=[CH:17][C:16]([NH:15][CH:9]([C:4]2[CH:3]=[C:2]([N:1]=[C:46]3[CH2:45][CH2:44][CH2:43][CH2:42][CH2:41][N:40]3[CH2:50][CH2:49][CH2:48][NH:47][C:25]3[N:30]=[CH:29][CH:28]=[CH:27][N:26]=3)[CH:7]=[C:6]([CH3:8])[CH:5]=2)[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:21][CH:20]=1)#[N:23]

Participants

6

Reactant 4

HCID 744042-ChloropyrimidineHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 81531DiisopropylethylamineHCID 86583556HCID 86583556, compound

Product 1

HCID 86583555HCID 86583555, compoundYield 23.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of the ethyl (RS)-(3-amino-5-methyl-phenyl)-(4-cyano-phenylamino)-acetate (475 mg, 1.54 mmol) obtained in Example 216.3, 2-chloropyrimidine (400 mg, 3.38 mmol), diisopropylethylamine (317 μl, 1.85 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (276 μl, 1.85 mmol) in THF (4 ml) was heated under reflux for 2 h. The reaction mixture was concentrated and the residue was purified by chromatography (SiO2, hexane/EtOAc 1:1->EtOAc). There were obtained 193 mg (23%) of ethyl (RS)-(4-cyano-phenylamino)-(3-methyl-5-{1-[3-(pyrimidin-2-ylamino)-propyl]-azepan-2-ylideneamino}-phenyl)-acetate as a yellowish foam; MS: 540 ([M+H]+).

Workup

  1. temperatureunder reflux for 2 h
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue was purified by chromatography (SiO2, hexane/EtOAc 1:1->EtOAc)

Sources & evidence

ORD record
ord-2fb32836a8804ebc9cbdf07faac3397c
Source dataset
uspto-grants-2006_07
Patent number
US07071212B2

Reaction notes

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