1,2-Dichloroethane → HCID 118023358, compound

HRID 2171823Notes

Reaction equation

HRID 2171823 reaction equation
[F:1][C:2]1([F: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][C:18]([CH3:23])([CH3:22])[CH2:19][O:20][CH3:21])[C:10]=3[CH:9]=2)[CH2:4][CH2:3]1.N1(CO)C2C=CC=C[C:30]=2N=N1.ClCCCl.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>O>[F:26][C:2]1([F:1])[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]([CH3:30])[C:18]([CH3:23])([CH3:22])[CH2:19][O:20][CH3:21])[C:10]=3[CH:9]=2)[CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 2241691H-Benzotriazole-1-methanolHCID 5049666Sodium triacetoxyborohydrideHCID 118023662HCID 118023662, compound

Product 1

HCID 118023358HCID 118023358, compoundYield 81.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of N-{[6-(4,4-difluorocyclohexyl)-2-methylthieno[2,3-d]pyrimidin-4-yl]methyl}-1-methoxy-2-methylpropan-2-amine (110 mg), 1H-benzotriazole-1-methanol (86 mg), and DCE was added NaBH(OAc)3 (182 mg), followed by stirring at room temperature for 4 hours. To the reaction mixture was added water, followed by extraction with EtOAc. The organic layer was washed with brine, dried over Na2SO4, and then concentrated under reduced pressure. The residue was purified by basic silica gel column (hexane/EtOAc) to obtain N-{[6-(4,4-difluorocyclohexyl)-2-methylthieno[2,3-d]pyrimidin-4-yl]methyl}-1-methoxy-N,2-dimethylpropan-2-amine (93 mg). This product was dissolved in MeOH, and fumaric acid (27 mg) was added thereto, followed by concentration under reduced pressure to obtain N-{[6-(4,4-difluorocyclohexyl)-2-methylthieno[2,3-d]pyrimidin-4-yl]methyl}-1-methoxy-N,2-dimethylpropan-2-aminefumarate (117 mg).

Workup

  1. extractionfollowed by extraction with EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by basic silica gel column (hexane/EtOAc)

Sources & evidence

ORD record
ord-e66b0fab1f79457d95d05a951b53dc62
Source dataset
uspto-grants-2015_06
Patent number
US09051339B2

Reaction notes

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