2-(2-((2-Chloro-5-methylpyrimidin-4-yl)ethynyl)phenyl)acetamide → 2-(2-(2-Chloro-5-methylpyrimidin-4-ylethyl)phenyl)acetamide

HRID 1778955Notes

Reaction equation

HRID 1778955 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]#[C:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH2:16][C:17]([NH2:19])=[O:18])[C:5]([CH3:20])=[CH:4][N:3]=1>CN(C=O)C.CO.[Pt]=O>[Cl:1][C:2]1[N:7]=[C:6]([CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH2:16][C:17]([NH2:19])=[O:18])[C:5]([CH3:20])=[CH:4][N:3]=1

Participants

5

Reactant 1

HCID 867126232-(2-((2-Chloro-5-methylpyrimidin-4-yl)ethynyl)phenyl)acetamide

Product 1

HCID 867126242-(2-(2-Chloro-5-methylpyrimidin-4-ylethyl)phenyl)acetamide

Reagents, catalysts & solvents 3

HCID 82844Platinum oxide (PtO)CatalystHCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

A suspension of 2-(2-((2-chloro-5-methylpyrimidin-4-yl)ethynyl)phenyl)acetamide (I9) (5.01 g, 17.5 mmol) in DMF (231 mL) and MeOH (80 mL) containing platinum oxide (0.995 g, 4.38 mmol) was stirred under a hydrogen atmosphere for 40 hours. The resulting mixture was filtered through a pad of Celite and the filtrate concentrated in vacuo. The resulting residue was diluted with ice water (400 mL) to give a precipitate, which was filtered and dried to give the title compound K6 (4.23 g, 83%); 1H NMR (300 MHz, d6-DMSO) δ 8.47 (s, 1H), 7.44 (brs, 1H), 7.21-7.24 (m, 1H), 7.12-7.15 (m, 3H), 6.92 (brs, 1H), 3.47 (s, 2H), 2.99 (s, 4H), 2.15 (s, 3H). LCMS-B: rt 5.528 min; m/z 290 [M+H]+.

Workup

  1. filtrationThe resulting mixture was filtered through a pad of Celite
  2. concentrationthe filtrate concentrated in vacuo
  3. additionThe resulting residue was diluted with ice water (400 mL)
  4. customto give a precipitate, which
  5. filtrationwas filtered
  6. customdried

Sources & evidence

ORD record
ord-4abd67c6083a47adaf4a7fcb118f1c0a
Source dataset
uspto-grants-2016_02
Patent number
US09266864B2

Reaction notes

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