Benzylacetylene → 2-(Methylthio)-6-benzyl-furano[2,3-d]pyrimidine

HRID 9764Notes

Reaction equation

HRID 9764 reaction equation
[CH3:1][S:2][C:3]1[N:8]=[C:7]([OH:9])[C:6](I)=[CH:5][N:4]=1.[C:11]1([CH2:17][C:18]#[CH:19])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(N(CC)CC)C.CN1C(=O)CCC1.C(OCC)(=O)C.[Cu]I.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:1][S:2][C:3]1[N:4]=[CH:5][C:6]2[CH:19]=[C:18]([CH2:17][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[O:9][C:7]=2[N:8]=1

Participants

8

Reactant 2

HCID 575753BenzylacetyleneHCID 178418710HCID 178418710, compound

Product 1

HCID 210399802-(Methylthio)-6-benzyl-furano[2,3-d]pyrimidine

Reagents, catalysts & solvents 5

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 2-methylthio-4-hydroxy-5-iodopyrimidine (2.65 g), 3-phenyl-1-propyne (1.49 mL), copper (I) iodide (90 mg) and bis(triphenylphosphine) Palladium (II) dichloride (Fluka, 160 mg) in 20 mL of triethylamine and NMP (7 mL) was stirred at 40° C. for 6 hours. The reaction mixture was diluted with ethyl acetate (100 mL), washed with brine (3×50 mL), concentrated and purified by column chromatography (5% EtOAc/hexanes) to give 0.57 g of a solid product. MP: 69–72.2° C. MS: 257.2 (M+H).

Workup

  1. washwashed with brine (3×50 mL)
  2. concentrationconcentrated
  3. custompurified by column chromatography (5% EtOAc/hexanes)

Sources & evidence

ORD record
ord-6762f22478744c559d8ab1ec0f6d6574
Source dataset
uspto-grants-2006_08
Patent number
US07091347B2

Reaction notes

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