Ethanol → 2-[[2-(5-Isopropylthieno[2,3-d]pyrimidin-4-yl)-2-azabicyclo[2.2.1]heptan-5-yl]oxy]ethanol

HRID 928566Notes

Reaction equation

HRID 928566 reaction equation
Cl[C:2]1[C:3]2[C:10]([CH:11]([CH3:13])[CH3:12])=[CH:9][S:8][C:4]=2[N:5]=[CH:6][N:7]=1.[CH:14]12[CH2:24][CH:17]([CH:18]([O:20][CH2:21][CH2:22][OH:23])[CH2:19]1)[CH2:16][NH:15]2.C(N(CC)CC)C.C(O)C>>[CH:11]([C:10]1[C:3]2[C:2]([N:15]3[CH2:16][CH:17]4[CH2:24][CH:14]3[CH2:19][CH:18]4[O:20][CH2:21][CH2:22][OH:23])=[N:7][CH:6]=[N:5][C:4]=2[S:8][CH:9]=1)([CH3:13])[CH3:12]

Participants

5

Reactant 4

HCID 702EthanolHCID 8471TriethylamineHCID 27576264-Chloro-5-isopropyl-thieno[2,3-D]pyrimidineHCID 895794962-(2-Azabicyclo[2.2.1]heptan-5-yloxy)ethanol

Product 1

HCID 895794632-[[2-(5-Isopropylthieno[2,3-d]pyrimidin-4-yl)-2-azabicyclo[2.2.1]heptan-5-yl]oxy]ethanol

Conditions

Temperature
50 °C

Procedure

4-Chloro-5-isopropyl-thieno[2,3-d]pyrimidine (0.35 g, 1.6 mmol), 2-(2-azabicyclo[2.2.1]heptan-5-yloxy)ethanol (0.39 g, 2.5 mmol), triethylamine (0.50 g, 0.70 mL, 4.9 mmol) and ethanol (3.95 g, 5 mL, 85.6 mmol) were combined and heated to 50° C. overnight. The reaction mixture was concentrated in vacuo. The resulting residue was taken up in DCM, washed with water, dried over Na2SO4 and concentrated in vacuo to afford

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. washwashed with water
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customto afford

Sources & evidence

ORD record
ord-1459f2b32ba24d53bd28067ae2f9fb3d
Source dataset
uspto-grants-2016_03
Patent number
US09290511B2

Reaction notes

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