Glycol monoethyl ether → HCID 57699670, compound

HRID 1010998Notes

Reaction equation

HRID 1010998 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.[CH2:24]([O:26][CH2:27][CH2:28][OH:29])[CH3:25]>>[CH2:24]([O:26][CH2:27][CH2:28][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)[CH3:25]

Participants

5

Reactant 4

HCID 8076Glycol monoethyl etherHCID 5462222PotassiumHCID 12476378Butan-1-olateHCID 127778192-Chloro-9-(tetrahydropyran-2-yl)adenine

Product 1

HCID 57699670HCID 57699670, compound

Conditions

Temperature
85 °C

Procedure

To a stirred solution of potassium t.butoxide (9.3 g, 82.8 mmol) in 1-ethoxy-2-ethanol (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 2 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 light brown solid, which was washed with petroleum ether, dried in vacuo (7.8 g, 92%).

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
  5. customto give a light brown solid, which
  6. washwas washed with petroleum ether
  7. customdried in vacuo (7.8 g, 92%)

Sources & evidence

ORD record
ord-616472f578cc4e80b959305fed022c54
Source dataset
uspto-grants-2011_07
Patent number
US07977344B2

Reaction notes

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