Hydrochloric Acid → (6-(4,4-Dimethylcyclohexyl)-2-methylthieno[2,3-d]pyrimidin-4-yl)methanol

HRID 2171780Notes

Reaction equation

HRID 2171780 reaction equation
[CH3:1][C:2]1([CH3:23])[CH2:7][CH2:6][CH:5]([C:8]2[S:22][C:11]3[N:12]=[C:13]([CH3:21])[N:14]=[C:15]([C:16](OCC)=[O:17])[C:10]=3[CH:9]=2)[CH2:4][CH2:3]1.[Cl-].[Ca+2].[Cl-].[BH4-].[Na+].Cl>CCOC(C)=O.O.CCO.C1COCC1>[CH3:1][C:2]1([CH3:23])[CH2:7][CH2:6][CH:5]([C:8]2[S:22][C:11]3[N:12]=[C:13]([CH3:21])[N:14]=[C:15]([CH2:16][OH:17])[C:10]=3[CH:9]=2)[CH2:4][CH2:3]1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 5284359Calcium ChlorideHCID 118024048Ethyl 6-(4,4-dimethylcyclohexyl)-2-methylthieno[2,3-d]pyrimidine-4-carboxylate

Product 1

HCID 118023561(6-(4,4-Dimethylcyclohexyl)-2-methylthieno[2,3-d]pyrimidin-4-yl)methanolYield 82.3%

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of ethyl 6-(4,4-dimethylcyclohexyl)-2-methylthieno[2,3-d]pyrimidine-4-carboxylate (13.0 g), THF (150 mL), and EtOH (150 mL) was added calcium chloride (6.6 g), followed by stirring at room temperature for 30 minutes and then adding NaBH4 (1.8 g) in small divided portions over 15 minutes under ice-cooling. After stirring at room temperature for 4.5 hours, to the reaction mixture were added water (100 mL) and EtOAc (100 mL) under ice-cooling. 1 M Hydrochloric acid (100 mL) was added thereto until the suspension became a solution, followed by concentration under reduced pressure and extracting with EtOAc. The organic layer was washed sequentially with water, saturated aqueous sodium bicarbonate, and brine, dried over MgSO4, and then concentrated under reduced pressure. The residue was purified by silica gel column (chloroform/EtOAc) to obtain [6-(4,4-dimethylcyclohexyl)-2-methylthieno[2,3-d]pyrimidin-4-yl]methanol (9.35 g).

Workup

  1. customover 15 minutes
  2. temperaturecooling
  3. stirringAfter stirring at room temperature for 4.5 hours, to the reaction mixture
  4. temperaturecooling
  5. concentrationfollowed by concentration under reduced pressure
  6. extractionextracting with EtOAc
  7. washThe organic layer was washed sequentially with water, saturated aqueous sodium bicarbonate, and brine
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by silica gel column (chloroform/EtOAc)

Sources & evidence

ORD record
ord-55daa947c9674fb1910271ff8da37200
Source dataset
uspto-grants-2015_06
Patent number
US09051339B2

Reaction notes

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