1-Methoxy-2-propanol → 2-{[1-Methyl-2-(methoxy)ethyl]oxy}-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine

HRID 1011004Notes

Reaction equation

HRID 1011004 reaction equation
[K].[O-]CCCC.Cl[C:8]1[N:16]=[C:15]2[C:11]([N:12]=[CH:13][N:14]2[CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][O:18]2)=[C:10]([NH2:23])[N:9]=1.[CH3:24][O:25][CH2:26][CH:27]([OH:29])[CH3:28]>>[CH3:28][CH:27]([O:29][C:8]1[N:16]=[C:15]2[C:11]([N:12]=[CH:13][N:14]2[CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][O:18]2)=[C:10]([NH2:23])[N:9]=1)[CH2:26][O:25][CH3:24]

Participants

5

Reactant 4

HCID 79001-Methoxy-2-propanolHCID 5462222PotassiumHCID 12476378Butan-1-olateHCID 127778192-Chloro-9-(tetrahydropyran-2-yl)adenine

Product 1

HCID 576996342-{[1-Methyl-2-(methoxy)ethyl]oxy}-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amineYield 84.7%

Conditions

Temperature
85 °C

Procedure

To a stirred solution of potassium t.butoxide (9.3 g, 82.8 mmol) in 1-methoxy-2-propanol (70 ml) was added 2-chloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine (7 g, 27.6 mmol). The mixture was heated to 80-90° C. for 4 h. Then most of the solvent was removed by evaporation under reduced pressure. The residue was partitioned between water and dichloromethane. The dichloromethane layer was separated, concentrated to give a brown oil (7.2 g, 84.7%).

Workup

  1. customThen most of the solvent was removed by evaporation under reduced pressure
  2. customThe residue was partitioned between water and dichloromethane
  3. customThe dichloromethane layer was separated
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-547a010ad50648109fb63c2d1b1f8c4a
Source dataset
uspto-grants-2011_07
Patent number
US07977344B2

Reaction notes

Loading…