Diisopropylethylamine → HCID 178518543, compound

HRID 474802Notes

Reaction equation

HRID 474802 reaction equation
[N:1]1[CH:6]=[C:5]([CH2:7][C:8]2[C:9](=[O:15])[NH:10][C:11](=[S:14])[NH:12][CH:13]=2)[CH:4]=[N:3][CH:2]=1.CCN(C(C)C)C(C)C.[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][C:33]2[CH:38]=[CH:37][C:36]([CH2:39]Cl)=[CH:35][CH:34]=2)=[CH:28][C:27]=1[C:41]([F:44])([F:43])[F:42]>C(Cl)Cl>[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][C:33]2[CH:34]=[CH:35][C:36]([CH2:39][S:14][C:11]3[NH:12][CH:13]=[C:8]([CH2:7][C:5]4[CH:6]=[N:1][CH:2]=[N:3][CH:4]=4)[C:9](=[O:15])[N:10]=3)=[CH:37][CH:38]=2)=[CH:28][C:27]=1[C:41]([F:42])([F:43])[F:44]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 109660395-(Pyrimid-5-ylmethyl)-2-thiouracilHCID 668255374-(Chloromethyl)phenyl 4-chloro-3-(trifluoromethyl)phenyl ether

Product 1

HCID 178518543HCID 178518543, compoundYield 26.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

To a suspension of 5-(5-pyrimidinylmethyl)-2-thioxo-2,3-dihydro-4(1H)-pyrimidinone (75 mg, 0.343 mmol) and DIPEA (0.163 ml, 0.934 mmol) in DCM (2 mL) was added 1-chloro-4-{[4-(chloromethyl)phenyl]oxy}-2-(trifluoromethyl)benzene (100 mg, 0.311 mmol). The solution was heated at 60° C. overnight. Purification via MDAP then afforded the title compound (42 mg, 26.7% yield). LCMS: rt=3.49 min, [M+H+]=505

Workup

  1. customPurification via MDAP

Sources & evidence

ORD record
ord-2547ab57502b4bbd83c0aea18a6aadcc
Source dataset
uspto-grants-2014_01
Patent number
US08637536B2

Reaction notes

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