Potassium Carbonate → 5-[3,4-Dimethoxy-5-(naphthalen-2-ylethynyl)-benzyl]-pyrimidine-2,4-diamine

HRID 963433

Reaction equation

HRID 963433 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:15]=[C:16](I)[C:17]=1[O:18][CH3:19])[CH2:6][C:7]1[C:8]([NH2:14])=[N:9][C:10]([NH2:13])=[N:11][CH:12]=1.[C:21]([C:23]1[CH:32]=[CH:31][C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=1)#[CH:22].C(=O)([O-])[O-].[K+].[K+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CN(C)C=O.[Cu]I.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:15]=[C:16]([C:22]#[C:21][C:23]2[CH:32]=[CH:31][C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH:24]=2)[C:17]=1[O:18][CH3:19])[CH2:6][C:7]1[C:8]([NH2:14])=[N:9][C:10]([NH2:13])=[N:11][CH:12]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 1150172-EthynylnaphthaleneHCID 111010945-(3,4-Dimethoxy-5-iodo-benzyl)pyrimidine-2,4-diamine

Product 1

HCID 190816585-[3,4-Dimethoxy-5-(naphthalen-2-ylethynyl)-benzyl]-pyrimidine-2,4-diamineYield 58%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 197 mg of 5-(3,4-dimethoxy-5-iodo-benzyl)pyrimidine-2,4-diamine, 155 mg of 2-ethynyl-naphthalene (Bull. Soc. Chim. Fr. [3], 7, 648, (1892)), 108 mg of potassium carbonate, 14 mg of triphenylphosphine and 5 mg of copper(I) iodide in 2 ml of dimethylformamide is heated at 100° for 4 hrs. The reaction mixture is cooled to room temperature, poured into 50 ml of water and extracted three times with 50 ml of methylene chloride each time. The organic phases are washed with 50 ml of water, dried over magnesium sulphate and concentrated. The crude product is recrystallized from ethyl acetate/n-hexane. 121 mg (58%) of 5-[3,4-dimethoxy-5-(naphthalen-2-ylethynyl)-benzyl]-pyrimidine-2,4-diamine are obtained as a yellowish solid. M.p. 152°-155°.

Workup

  1. temperatureis heated at 100° for 4 hrs
  2. extractionextracted three times with 50 ml of methylene chloride each time
  3. washThe organic phases are washed with 50 ml of water
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated
  6. customThe crude product is recrystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-2cdae77e1559449aab36177774fa590d
Source dataset
uspto-grants-1998_06
Patent number
US05763450

Linked notes

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