3-Hydroxypyridine → HCID 86618447, compound

HRID 2262246Notes

Reaction equation

HRID 2262246 reaction equation
[OH:1][C:2]1[CH:3]=N[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].Br[CH2:11][C:12]1[S:20][C:19]2[C:18]([N:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)=[N:17][C:16]([Cl:27])=[N:15][C:14]=2[CH:13]=1.[CH2:28]1COCC1>>[Cl:27][C:16]1[N:17]=[C:18]([N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)[C:19]2[S:20][C:12]([CH2:11][O:1][C:2]3[CH:3]=[CH:28][CH:5]=[CH:6][CH:7]=3)=[CH:13][C:14]=2[N:15]=1

Participants

5

Reactant 4

HCID 79713-HydroxypyridineHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 461807264-(6-(Bromomethyl)-2-chlorothieno[3,2-d]pyrimidin-4-yl)morpholine

Product 1

HCID 86618447HCID 86618447, compound

Procedure

To a solution of 3-hydroxypyridine (102 mg) in THF (10 mL) was added sodium hydride (43 mg) and the reaction stirred at room temperature for 1 h. Then, 6-bromomethyl-2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidine (150 mg) was added and the reaction stirred at room temperature for 16 h. The reaction was quenched with water (20 mL) and extracted into ethyl acetate (2×20 mL). The combined organics were washed with aqueous brine solution (2×20 mL), dried (MgSO4), reduced in vacuo and purified by column chromatography to give 2-chloro-4-morpholin-4-yl-6-phenoxymethyl-thieno[3,2-d]pyrimidine as a white solid.

Workup

  1. stirringthe reaction stirred at room temperature for 16 h
  2. customThe reaction was quenched with water (20 mL)
  3. extractionextracted into ethyl acetate (2×20 mL)
  4. washThe combined organics were washed with aqueous brine solution (2×20 mL)
  5. dry with materialdried (MgSO4)
  6. custompurified by column chromatography

Sources & evidence

ORD record
ord-53fdb5d397034c40a9c520cfcf8b603f
Source dataset
uspto-grants-2010_12
Patent number
US07846929B2

Reaction notes

Loading…