Sulfuric Acid → 1-{2-[6-Amino-8-(3-fluorophenyl)-9-methyl-9H-2-purinyl}-1-ethynyl]-1-cyclopentanol Sulfate

HRID 1826537Notes

Reaction equation

HRID 1826537 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]([C:11]#[C:12][C:13]2([OH:18])[CH2:17][CH2:16][CH2:15][CH2:14]2)[N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=1)[N:6]2[CH3:19].[S:27](=O)(=[O:30])([OH:29])[OH:28]>CO>[S:27]([O:18][C:13]1([C:12]#[C:11][C:9]2[N:8]=[C:7]3[C:3]([N:4]=[C:5]([C:20]4[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=4)[N:6]3[CH3:19])=[C:2]([NH2:1])[N:10]=2)[CH2:14][CH2:15][CH2:16][CH2:17]1)([OH:30])(=[O:29])=[O:28]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 98413641-(2-(6-amino-8-(3-fluorophenyl)-9-methyl-9H-2-purinyl)-1-ethynyl)-1-cyclopentanol

Product 1

HCID 1317257681-{2-[6-Amino-8-(3-fluorophenyl)-9-methyl-9H-2-purinyl}-1-ethynyl]-1-cyclopentanol SulfateYield 92.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

1-{2-(6-Amino-8-(3-fluorophenyl)-9-methyl-9H-2-purinyl]-1-ethynyl}-1-cyclopentanol (1.59 g) was suspended in 10 mL of methanol and 1 mL of a methanol solution of 440 mg of concentrated sulfuric acid was added dropwise thereinto at room temperature. The resulting solution was evaporated until the amount of the solution became about one half followed by adding 4 mL of ether thereto. The resulting crystals were collected by filtration, washed with ether and dried to give 1.79 g of the sulfate.

Workup

  1. customat room temperature
  2. customThe resulting solution was evaporated until the amount of the solution
  3. additionby adding 4 mL of ether
  4. filtrationThe resulting crystals were collected by filtration
  5. washwashed with ether
  6. customdried

Sources & evidence

ORD record
ord-8236b476725a4210b2d57acb737bd0d9
Source dataset
uspto-grants-2006_05
Patent number
USRE039112E1

Reaction notes

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