Dimethylformamide → HCID 118023980, compound

HRID 2171801Notes

Reaction equation

HRID 2171801 reaction equation
[CH3:1][C:2]1([CH3:25])[CH2:7][CH2:6][CH:5]([C:8]2[S:24][C:11]3[N:12]=[C:13]([CH3:23])[N:14]=[C:15]([CH2:16][NH:17][CH:18]4[CH2:22][CH2:21][CH2:20][CH2:19]4)[C:10]=3[CH:9]=2)[CH2:4][CH2:3]1.CN(C=O)C.Br[CH2:32][CH2:33][CH2:34][OH:35].C([O-])([O-])=O.[Na+].[Na+]>O>[CH:18]1([N:17]([CH2:16][C:15]2[C:10]3[CH:9]=[C:8]([CH:5]4[CH2:6][CH2:7][C:2]([CH3:25])([CH3:1])[CH2:3][CH2:4]4)[S:24][C:11]=3[N:12]=[C:13]([CH3:23])[N:14]=2)[CH2:32][CH2:33][CH2:34][OH:35])[CH2:19][CH2:20][CH2:21][CH2:22]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 123083-Bromo-1-propanolHCID 118023630HCID 118023630, compound

Product 1

HCID 118023980HCID 118023980, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of N-{[6-(4,4-dimethylcyclohexyl)-2-methylthieno[2,3-d]pyrimidin-4-yl]methyl}cyclopentaneamine (128 mg) and DMF (3 mL) were added 3-bromopropan-1-ol (100 μL) and Na2CO3 (110 mg), followed by stirring at 100° C. for 15 hours. The reaction mixture was cooled to room temperature and then water was added thereto, followed by extraction with EtOAc. The organic layer was dried over MgSO4 and then concentrated under reduced pressure. The residue was purified by basic silica gel column (hexane/EtOAc) to obtain 3-(cyclopentyl{[6-(4,4-dimethylcyclohexyl)-2-methylthieno[2,3-d]pyrimidin-4-yl]methyl}amino)propan-1-ol (88 mg).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionfollowed by extraction with EtOAc
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by basic silica gel column (hexane/EtOAc)

Sources & evidence

ORD record
ord-f47aa74b6d9b4eaca5c478ac55ad4408
Source dataset
uspto-grants-2015_06
Patent number
US09051339B2

Reaction notes

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