Cesium carbonate → HCID 67191479, compound

HRID 2359647Notes

Reaction equation

HRID 2359647 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7](Cl)=[N:8][C:9]([C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)=[N:10][CH:11]=1)=[O:5])[CH3:2].[C:19]([C:21]1[CH:22]=[C:23]([OH:27])[CH:24]=[CH:25][CH:26]=1)#[N:20].C([O-])([O-])=O.[Cs+].[Cs+]>CC#N>[CH2:1]([O:3][C:4]([C:6]1[C:7]([O:27][C:23]2[CH:24]=[CH:25][CH:26]=[C:21]([C:19]#[N:20])[CH:22]=2)=[N:8][C:9]([C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)=[N:10][CH:11]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 133943-CyanophenolHCID 24903914Ethyl 4-chloro-2-(pyridin-3-yl)pyrimidine-5-carboxylate

Product 1

HCID 67191479HCID 67191479, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of Compound 14d (1.0 g; 3.79 mmol), 3-cyanophenol (0.587 g; 4.93 mmol) and Cs2CO3 (4.93 g; 15.13 mmol) in CH3CN (25 mL) was stirred at room temperature for 2 h. The suspension was poured into ice-water and extracted with CH2Cl2 (3×50 mL). The combined organic phases were dried over MgSO4 and concentrated to afford Compound 14e. 1H NMR (300 MHz, CDCl3): δ 9.40 (s, 1H), 9.25 (s, 1H), 8.70 (d, 1H), 8.45 (m, 1H), 7.45-7.65 (m, 4H), 7.35 (m, 1H), 4.50 (q, 2H), 1.45 (t, 3H); MS: m/z 347.2 (M+H)+.

Workup

  1. extractionextracted with CH2Cl2 (3×50 mL)
  2. dry with materialThe combined organic phases were dried over MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-221de8aebe90472b8a1aaa864bc75555
Source dataset
uspto-grants-2014_04
Patent number
US08685990B2

Reaction notes

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