Water → HCID 19071345, compound

HRID 1955617Notes

Reaction equation

HRID 1955617 reaction equation
Cl[C:2]1[C:7]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[C:6]([S:13][CH3:14])[N:5]=[C:4]([CH3:15])[N:3]=1.C(=O)([O-])[O-].[K+].[K+].[C:22]([C:24]1[CH:37]=[CH:36][CH:35]=[CH:34][C:25]=1[O:26][C:27]1[CH:28]=[C:29]([OH:33])[CH:30]=[CH:31][CH:32]=1)#[N:23].O>CN(C=O)C.[Cu](I)I>[CH3:15][C:4]1[N:5]=[C:6]([S:13][CH3:14])[C:7]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[C:2]([O:33][C:29]2[CH:30]=[CH:31][CH:32]=[C:27]([O:26][C:25]3[CH:34]=[CH:35][CH:36]=[CH:37][C:24]=3[C:22]#[N:23])[CH:28]=2)[N:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 19071337HCID 19071337, compoundHCID 19071348HCID 19071348, compound

Product 1

HCID 19071345HCID 19071345, compound

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 6228DimethylformamideSolvent2×

Procedure

A solution of methyl 2-(4-chloro-2-methyl-6-methylthio-pyrimidin-5-yl)-acetate (5.5 g) in DMF (80 ml) is added to a suspension of anhydrous potassium carbonate (5.6 g) and 3-(2-cyanophenoxy)phenol (5.1 g) and copper iodide (1 g) in DMF at room temperature. The mixture was heated to +120° C. for 2 hours and then cooled. The mixture is poured into water and extracted successively with ethyl acetate (2×50 ml) and the organic phase dried over anhydrous sodium sulfate. Evaporation and drying under high vacuum gives the methyl 2-[2-methyl-4-methylthio-6-(3-(2-cyanophenoxy)-phenoxy)-pyrimidin-5-yl]-acetate, as a crude product in form of a yellow oil. NMR (CDCl3): 6.18-6.84 (m, 3H); 3.74 (s, 2H); 3.69 (s, 3H); 2.85 (m, 1H); 2.51 (s, 3H); 2.45 (s, 3H); 2.34 (s, 3H); 1.22 (d, 6H).

Workup

  1. temperatureThe mixture was heated to +120° C. for 2 hours
  2. temperaturecooled
  3. extractionextracted successively with ethyl acetate (2×50 ml)
  4. dry with materialthe organic phase dried over anhydrous sodium sulfate
  5. customEvaporation
  6. customdrying under high vacuum

Sources & evidence

ORD record
ord-948808994ada417e8bfc06fee9559df0
Source dataset
uspto-grants-1998_07
Patent number
US05776941

Reaction notes

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