Diisopropylethylamine → HCID 178494156, compound

HRID 474818Notes

Reaction equation

HRID 474818 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][C:7]2[CH:14]=[CH:13][C:12]([CH2:15]Cl)=[CH:11][C:8]=2[C:9]#[N:10])=[CH:4][C:3]=1[C:19]([F:22])([F:21])[F:20].[CH3:23][O:24][C:25]1[N:30]=[CH:29][C:28]([CH2:31][C:32]2[C:33](=[O:39])[NH:34][C:35](=[S:38])[NH:36][CH:37]=2)=[CH:27][N:26]=1.CCN(C(C)C)C(C)C>ClCCCl>[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][C:7]2[CH:14]=[CH:13][C:12]([CH2:15][S:38][C:35]3[NH:36][CH:37]=[C:32]([CH2:31][C:28]4[CH:29]=[N:30][C:25]([O:24][CH3:23])=[N:26][CH:27]=4)[C:33](=[O:39])[N:34]=3)=[CH:11][C:8]=2[C:9]#[N:10])=[CH:4][C:3]=1[C:19]([F:22])([F:21])[F:20]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 219362445-(2-Methoxypyrimidin-5-ylmethyl)-2-thiouracilHCID 677735002-(4-Chloro-3-(trifluoromethyl)phenoxy)-5-(chloromethyl)benzonitrile

Product 1

HCID 178494156HCID 178494156, compoundYield 21.64%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

The same procedure as E63 from 2-(4-chloro-3-(trifluoromethyl)phenoxy)-5-(chloromethyl)benzonitrile (200 mg, 0.578 mmol), 5-{[2-(methyloxy)-5-pyrimidinyl]methyl}-2-thioxo-2,3-dihydro-4(1H)-pyrimidinone (174 mg, 0.693 mmol) and DIPEA (0.303 mL, 1.733 mmol) in DCE (3.0 mL), except that the reaction time was prolonged to 1.5 h, to afford the title compound (70 mg, 21.64% yield). LCMS: rt=3.44 min, [M+H+]=560

Sources & evidence

ORD record
ord-8e57040a0dd449a4ac999cb035c2c95a
Source dataset
uspto-grants-2014_01
Patent number
US08637536B2

Reaction notes

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