Methyl iodide → HCID 86618738, compound

HRID 1747693Notes

Reaction equation

HRID 1747693 reaction equation
[Cl:1][C:2]1[C:7]([NH:8][C:9](=[O:16])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[C:6]([Cl:17])[N:5]=[CH:4][N:3]=1.O1CCC[CH2:19]1.C(=O)([O-])[O-].[Cs+].[Cs+].CI>>[Cl:17][C:6]1[C:7]([N:8]([CH3:19])[C:9](=[O:16])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[C:2]([Cl:1])[N:3]=[CH:4][N:5]=1

Participants

5

Reactant 4

HCID 6328Methyl iodide2×HCID 8028TetrahydrofuranHCID 10796Cesium carbonate2×HCID 12611968HCID 12611968, compound

Product 1

HCID 86618738HCID 86618738, compound

Procedure

To a solution of N-(4,6-dichloropyrimidin-5-yl)benzamide (3.0 g, 0.011 mol) in tetrahydrofuran (70 mL, 0.9 mol) was added cesium carbonate (9.8 g, 0.030 mol). The suspension was stirred for 5 minutes and to this was added methyl iodide (1.4 mL, 0.022 mol) (purified on aluminum oxide). After stirring for 1 hour, cesium carbonate (5.0 g, 0.015 mol) and methyl iodide (0.70 mL, 0.011 mol) (purified on alumina) were added. The reaction was stirred for 2 hours, quenched by addition of saturated aqueous NH4Cl, and the mixture was extracted with ethyl acetate, washed with water, brine, dried (Na2SO4), filtered, concentrated and trituration in diethyl ether to obtain 2.54 g (80%).

Workup

  1. stirringAfter stirring for 1 hour
  2. stirringThe reaction was stirred for 2 hours
  3. customquenched by addition of saturated aqueous NH4Cl
  4. extractionthe mixture was extracted with ethyl acetate
  5. washwashed with water, brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customtrituration in diethyl ether to obtain 2.54 g (80%)

Sources & evidence

ORD record
ord-17671a2a46154540a35eb1ffaff6dd5b
Source dataset
uspto-grants-2015_10
Patent number
US09150525B2

Reaction notes

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