Hydrogen Peroxide → 2-(2-Chloro-4-morpholinothieno[3,2-d]pyrimidin-7-yl)ethanol

HRID 334154Notes

Reaction equation

HRID 334154 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[C:5]2[S:10][CH:9]=[C:8]([CH:11]=[CH2:12])[C:6]=2[N:7]=1.[O:19]1CCCC1.B1C2CCCC1CCC2.OO.[OH-].[Na+]>O>[Cl:1][C:2]1[N:3]=[C:4]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[C:5]2[S:10][CH:9]=[C:8]([CH2:11][CH2:12][OH:19])[C:6]=2[N:7]=1

Participants

7

Reactant 5

HCID 784Hydrogen PeroxideHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 789669-Borabicyclo(3.3.1)nonane2×HCID 706766054-(2-Chloro-7-vinylthieno[3,2-d]pyrimidin-4-yl)morpholine

Product 1

HCID 706767712-(2-Chloro-4-morpholinothieno[3,2-d]pyrimidin-7-yl)ethanolYield 61.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

4-(2-chloro-7-vinylthieno[3,2-d]pyrimidin-4-yl)morpholine (170 mg, 0.6 mmol) was dissolved in tetrahydrofuran (10 mL, 100 mmol) and cooled to 0° C. under an atmosphere of nitrogen. 0.5 M 9-BBN in hexanes (3.4 mL, 2 mmol) was added and the reaction was allowed to warm up to room temperature and stir overnight. LCMS indicated mostly starting material so the reaction was cooled to 0° C. again and added 0.5 M 9-BBN in hexanes (8.0 mL, 4 mmol) and allowed to warm up to room temperature and stir overnight again. Added 20 M hydrogen peroxide (1.4 mL, 20 mmol) followed by 5 M sodium hydroxide in water (2.4 mL, 10 mmol). The reaction was diluted with water and extracted with ethyl acetate, dried over magnesium sulfate and concentrated in vacuo and was purified by silica gel chromatography (0 to 50% ethyl acetate/heptanes) on the CombiFlash® Rf system and concentrated in vacuo to give 2-(2-chloro-4-morpholinothieno[3,2-d]pyrimidin-7-yl)ethanol (110 mg, 61% yield)

Workup

  1. temperatureto warm up to room temperature
  2. temperaturewas cooled to 0° C. again
  3. temperatureto warm up to room temperature
  4. stirringstir overnight again
  5. extractionextracted with ethyl acetate
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customwas purified by silica gel chromatography (0 to 50% ethyl acetate/heptanes) on the CombiFlash® Rf system
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2ca0aed412274a3f9868a3f139e50632
Source dataset
uspto-grants-2014_11
Patent number
US08883799B2

Reaction notes

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