Ethanol → HCID 73446453, compound

HRID 1271042Notes

Reaction equation

HRID 1271042 reaction equation
[Cl:1][C:2]1[C:7](I)=[CH:6][N:5]=[C:4]([N:9]=[CH:10][N:11]([CH3:13])[CH3:12])[N:3]=1.C(O)C.[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]#[CH:25])=[CH:20][CH:19]=1>[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(N(CC)CC)C>[Cl:1][C:2]1[C:7]([C:25]#[C:24][C:21]2[CH:22]=[CH:23][C:18]([Cl:17])=[CH:19][CH:20]=2)=[CH:6][N:5]=[C:4]([N:9]=[CH:10][N:11]([CH3:13])[CH3:12])[N:3]=1

Participants

7

Reactant 3

HCID 702EthanolHCID 70118Benzene, 1-chloro-4-ethynyl-HCID 71350792N'-(4-Chloro-5-iodopyrimidin-2-yl)-N,N-dimethylmethanimidamide

Product 1

HCID 73446453HCID 73446453, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Procedure

A 1-liter, 3-neck-round-bottom flask was equipped with an air stirrer, reflux condenser, and a nitrogen inlet. The 4-chloro-2-(dimethylaminomethyleneamino)-5-iodopyrimidine (65.2 g), ethanol (84 mL), and triethylamine (336 mL) were charged and heated to reflux. Copper (I) iodide (105 mg) and dichlorobis(triphenyl)phosphine palladium II (386 mg) were added. Neat 1-chloro-4-ethynylbenzene (30.1 g) was added and the mixture was refluxed approximately 2.5 hours. The mixture was cooled to ambient temperature, stirred for 1.5 hours and filtered. The filter cake was slurried in water:ethanol (4:1 v/v, 120 mL), filtered and dried in vacuo at 50° C. to give 4-chloro-5-(4-chlorophenylethynyl)-2-dimethylaminomethyleneaminopyrimidine as a yellow solid: 55.7 g m.p. 195–197° C.

Workup

  1. customA 1-liter, 3-neck-round-bottom flask was equipped with an air stirrer
  2. temperaturereflux condenser, and a nitrogen inlet
  3. temperatureheated to reflux
  4. temperaturethe mixture was refluxed approximately 2.5 hours
  5. filtrationfiltered
  6. filtrationfiltered
  7. customdried in vacuo at 50° C.

Sources & evidence

ORD record
ord-d8842b55cf574be0936fb79139e611d1
Source dataset
uspto-grants-2007_04
Patent number
US07205297B2

Reaction notes

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