5-Bromo-2-iodopyrimidine → 5-Bromo-2-{4-[3-(6-methylpyridin-2-yl)prop-2-yn-1-ylidene]piperidin-1-yl}pyrimidine

HRID 1895985Notes

Reaction equation

HRID 1895985 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]#[C:9][CH:10]=[C:11]2[CH2:16][CH2:15][N:14](C3C=CC=CN=3)[CH2:13][CH2:12]2)[N:3]=1.[Br:23][C:24]1[CH:25]=[N:26][C:27](I)=[N:28][CH:29]=1>CN(C)C(=O)C>[Br:23][C:24]1[CH:25]=[N:26][C:27]([N:14]2[CH2:15][CH2:16][C:11](=[CH:10][C:9]#[C:8][C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[N:3]=3)[CH2:12][CH2:13]2)=[N:28][CH:29]=1

Participants

4

Reactant 2

HCID 70066515-Bromo-2-iodopyrimidineHCID 251816392-Methyl-6-[3-(1-pyridin-2-ylpiperidin-4-ylidene)prop-1-yn-1-yl]pyridine

Product 1

HCID 875512135-Bromo-2-{4-[3-(6-methylpyridin-2-yl)prop-2-yn-1-ylidene]piperidin-1-yl}pyrimidineYield 64.1%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

The title compound was prepared following the procedure described for the compound of Example 59, but substituting NMP with N,N-dimethylacetamide and substituting 2-fluoropyridine with 5-bromo-2-iodopyrimidine and reacting the mixture at r.t. Purification was carried out by automated flash liquid chromatography (Horizon™-Biotage) eluting with CHCl3-1.4 N MeOH NH3 100:0.5. White solid. Yield: 64.1%.

Workup

  1. customat r.t
  2. customPurification
  3. washeluting with CHCl3-1.4 N MeOH NH3 100:0.5

Sources & evidence

ORD record
ord-88b19d9381ff4c698f6c277232963d01
Source dataset
uspto-grants-2013_08
Patent number
US08518916B2

Reaction notes

Loading…