Hydrochloric Acid → HCID 118023920, compound

HRID 2171779Notes

Reaction equation

HRID 2171779 reaction equation
[CH:1]1([C:7]2[S:21][C:10]3[N:11]=[C:12]([CH3:20])[N:13]=[C:14]([C:15](OCC)=[O:16])[C:9]=3[CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl-].[Ca+2].[Cl-].[BH4-].[Na+].Cl>CCO.C1COCC1>[CH:1]1([C:7]2[S:21][C:10]3[N:11]=[C:12]([CH3:20])[N:13]=[C:14]([CH2:15][OH:16])[C:9]=3[CH:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 5284359Calcium ChlorideHCID 118023558HCID 118023558, compound

Product 1

HCID 118023920HCID 118023920, compoundYield 50.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of ethyl 6-cyclohexyl-2-methylthieno[2,3-d]pyrimidine-4-carboxylate (29.3 g), calcium chloride (18 g), and THF (200 mL) was added NaBH4 (5.5 g) in small divided portions at room temperature, and then EtOH (200 mL) was slowly added thereto over 5 minutes, followed by stirring at room temperature for 4 hours. To the reaction mixture was added ice water, followed by stirring, adding 1 M hydrochloric acid until the suspension becomes a solution state, and then extracting with EtOAc. The organic layer was washed sequentially with water, saturated aqueous sodium bicarbonate, and brine. To the organic layer were added MgSO4, activated carbon, and basic silica gel, followed by stirring. The mixture was filtered through Celite and then concentrated under reduced pressure. The residue was purified by silica gel column (chloroform/EtOAc) to obtain (6-cyclohexyl-2-methylthieno[2,3-d]pyrimidin-4-yl)methanol (12.7 g).

Workup

  1. customat room temperature
  2. stirringby stirring
  3. extractionextracting with EtOAc
  4. washThe organic layer was washed sequentially with water, saturated aqueous sodium bicarbonate, and brine
  5. additionTo the organic layer were added MgSO4, activated carbon, and basic silica gel
  6. stirringby stirring
  7. filtrationThe mixture was filtered through Celite
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column (chloroform/EtOAc)

Sources & evidence

ORD record
ord-248a6a836ada48b7adc705df6fbf05f7
Source dataset
uspto-grants-2015_06
Patent number
US09051339B2

Reaction notes

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