Acetonitrile → HCID 25055624, compound

HRID 1365882Notes

Reaction equation

[C:1]([C:3]1[CH:4]=[N:5][C:6]([NH2:9])=[N:7][CH:8]=1)#[CH:2].I[C:11]1[C:12](=[O:28])[N:13]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=2)[CH:14]=[CH:15][C:16]=1[CH3:17].CC#N.C(N(CC)CC)C>CCOC(C)=O.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[NH2:9][C:6]1[N:7]=[CH:8][C:3]([C:1]#[C:2][C:11]2[C:12](=[O:28])[N:13]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:25])[F:26])[CH:19]=3)[CH:14]=[CH:15][C:16]=2[CH3:17])=[CH:4][N:5]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a mixture of 5-ethynylpyrimidin-2-amine (0.023 g, 0.19 mmol), 3-iodo-4-methyl-1-(3-(trifluoromethyl)phenyl)pyridin-2(1H)-one (0.041 g, 0.11 mmol), copper(I) iodide (0.001 g, 0.0054 mmol), and Pd(PPh3)2Cl2 (0.004 g, 0.0054 mmol) was added MeCN (2 mL) and triethylamine (0.300 ml, 2.200 mmol). The mixture was heated to 80° C. in a resealable tube. After 16 hrs, the reaction mixture was diluted with EtOAc and washed with water and brine. After concentrating in vacuo, the crude residue was purified by silica gel chromatography using 30-100% hexanes:EtOAc to afford 3-((2-amino-5-pyrimidinyl)ethynyl)-4-methyl-1-(3-(trifluoromethyl)phenyl)-2(1H)-pyridinone as a white solid. Found M+H+=371.2.

Workup

washwashed with water and brine
concentrationAfter concentrating in vacuo
customthe crude residue was purified by silica gel chromatography

Sources & evidence

ORD record: ord-0d0533f32ee347609973fdfaf746ed96
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07893061B2

Reaction notes

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