1,4-Dioxane → 4-(2-Chloro-7-vinylthieno[3,2-d]pyrimidin-4-yl)morpholine

HRID 334153Notes

Reaction equation

HRID 334153 reaction equation
Br[C:2]1[C:6]2[N:7]=[C:8]([Cl:17])[N:9]=[C:10]([N:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)[C:5]=2[S:4][CH:3]=1.O1CCO[CH2:20][CH2:19]1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:17][C:8]1[N:9]=[C:10]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[C:5]2[S:4][CH:3]=[C:2]([CH:19]=[CH2:20])[C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 312751,4-DioxaneHCID 534387087-Bromo-2-chloro-4-(4-morpholinyl)-thieno[3,2-d]pyrimidine

Product 1

HCID 706766054-(2-Chloro-7-vinylthieno[3,2-d]pyrimidin-4-yl)morpholineYield 39.5%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
100 °C

Procedure

4-(7-bromo-2-chlorothieno[3,2-d]pyrimidin-4-yl)morpholine (3.55 g, 10.6 mmol), (2-Ethenyl)tri-n-butyltin (3.41 mL, 11.7 mmol), Pd(PPh3)4 (613 mg, 0.53 mmol), and 1,4-Dioxane (30 mL, 400 mmol) were combined in a sealed tube and heated at 100° C. 19.5 h. Complete reaction was confirmed by LCMS. Concentrated in vacuo and purified by silica gel chromatography (0 to 50% ethyl acetate/heptanes) on the CombiFlash® Rf system and concentrated in vacuo to give 4-(2-chloro-7-vinylthieno[3,2-d]pyrimidin-4-yl)morpholine (1.18 g, 39.5% yield)

Workup

  1. custom19.5 h
  2. customComplete reaction
  3. concentrationConcentrated in vacuo
  4. custompurified by silica gel chromatography (0 to 50% ethyl acetate/heptanes) on the CombiFlash® Rf system
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-478cbca551254b3482e017c4823894d9
Source dataset
uspto-grants-2014_11
Patent number
US08883799B2

Reaction notes

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