1,2-Dichloroethane → HCID 118023873, compound

HRID 2171825Notes

Reaction equation

HRID 2171825 reaction equation
[CH3:1][C:2]1([CH3:26])[CH2:7][CH2:6][CH:5]([C:8]2[S:25][C:11]3[N:12]=[C:13]([CH3:24])[N:14]=[C:15]([CH2:16][NH:17][CH:18]4[CH2:23][CH2:22][O:21][CH2:20][CH2:19]4)[C:10]=3[CH:9]=2)[CH2:4][CH2:3]1.[O:27]1CC(O)O[CH2:29][CH:28]1O.ClCCCl.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>CCOC(C)=O.O.CO>[CH3:1][C:2]1([CH3:26])[CH2:7][CH2:6][CH:5]([C:8]2[S:25][C:11]3[N:12]=[C:13]([CH3:24])[N:14]=[C:15]([CH2:16][N:17]([CH:18]4[CH2:23][CH2:22][O:21][CH2:20][CH2:19]4)[CH2:29][CH2:28][OH:27])[C:10]=3[CH:9]=2)[CH2:4][CH2:3]1

Participants

8

Reactant 4

HCID 111,2-DichloroethaneHCID 186078Glycolaldehyde dimerHCID 5049666Sodium triacetoxyborohydrideHCID 118023960HCID 118023960, compound

Product 1

HCID 118023873HCID 118023873, compoundYield 45.6%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of N-{[6-(4,4-dimethylcyclohexyl)-2-methylthieno[2,3-d]pyrimidin-4-yl]methyl}tetrahydro-2H-pyran-4-amine (100 mg), 1,4-dioxane-2,5-diol (64 mg), DCE (2 mL), and MeOH (1 mL) was added NaBH(OAc)3 (170 mg) under ice-cooling, followed by stirring at 0° C. for 1 hour. To the reaction mixture were added water and EtOAc, followed by extraction with EtOAc. The organic layer was washed with brine, dried, and then concentrated under reduced pressure. The residue was purified by silica gel column to obtain 2-[{[6-(4,4-dimethylcyclohexyl)-2-methylthieno[2,3-d]pyrimidin-4-yl]methyl}(tetrahydro-2H-pyran-4-yl)amino]ethanol (51 mg).

Workup

  1. temperaturecooling
  2. extractionfollowed by extraction with EtOAc
  3. washThe organic layer was washed with brine
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column

Sources & evidence

ORD record
ord-8c4025ca65d9406d985eb48d7b1a77c0
Source dataset
uspto-grants-2015_06
Patent number
US09051339B2

Reaction notes

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