Cyclopropylacetylene → HCID 86665091, compound

HRID 1038802Notes

Reaction equation

HRID 1038802 reaction equation
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[O:10][CH:9]=[CH:8][C:6]=2[N:7]=1.[C:12]([CH:14]1[CH2:16][CH2:15]1)#[CH:13]>C1COCC1.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.[Cu]I.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:1][C:2]1[N:3]=[C:4]([C:13]#[C:12][CH:14]2[CH2:16][CH2:15]2)[C:5]2[O:10][CH:9]=[CH:8][C:6]=2[N:7]=1

Participants

7

Reactant 2

HCID 138823CyclopropylacetyleneHCID 457899682,4-Dichlorofuro[3,2-D]pyrimidine

Product 1

HCID 86665091HCID 86665091, compoundYield 26%

Reagents, catalysts & solvents 4

HCID 11776TriphenylphosphineCatalystHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a flask was added 2,4-dichlorofuro[3,2-d]pyrimidine (0.30 g, 1.6 mmol, ArkPharm), PPh3 (0.008 g, 0.03 mmol) in THF (1.2 mL) and TEA (1.764 mL). The mixture was placed under vacuum and purged with N2 three times, then Pd(PPh3)2Cl2 (0.011 g, 0.016 mmol) and CuI (0.006 g, 0.03 mmol) were added. The mixture was placed under vacuum and purged with N2 three times and then ethynylcyclopropane (0.161 mL, 1.905 mmol) was added. The mixture was placed under vacuum and purged with N2 and then the mixture was stirred at rt for about 18 h. The mixture was filtered and the filter cake was washed with EtOAc (3×20 mL). The filtrate was concentrated under reduced pressure and the residue was deposited on silica gel and purified by column chromatography (12 g silica gel, 0 to 30% EtOAc/heptane) to give 2-chloro-4-(cyclopropylethynyl)furo[3,2-d]pyrimidine (0.090 g, 26%): LC/MS (Table 2, Method c) Rt=2.11 min; MS m/z 219 (M+H)+.

Workup

  1. custompurged with N2 three times
  2. custompurged with N2 three times
  3. custompurged with N2
  4. filtrationThe mixture was filtered
  5. washthe filter cake was washed with EtOAc (3×20 mL)
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. custompurified by column chromatography (12 g silica gel, 0 to 30% EtOAc/heptane)

Sources & evidence

ORD record
ord-b5a6f79525ee4f09bd0e73d8906e7f3c
Source dataset
uspto-grants-2013_10
Patent number
US08551981B2

Reaction notes

Loading…