Trifluoroacetic acid → [4-(4-{2-[6-Amino-8-methoxy-2-(2-methoxyethoxy)purin-9-yl]ethyl}-piperidin-1-ylmethyl)phenyl]methanol

HRID 1666203Notes

Reaction equation

HRID 1666203 reaction equation
C(O[C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][N:16]2[C:24]([O:25][CH3:26])=[N:23][C:22]3[C:17]2=[N:18][C:19]([O:28][CH2:29][CH2:30][O:31][CH3:32])=[N:20][C:21]=3[NH2:27])[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O.ClC[C:42]1[CH:49]=[CH:48][C:45]([CH2:46][OH:47])=[CH:44][CH:43]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[NH2:27][C:21]1[N:20]=[C:19]([O:28][CH2:29][CH2:30][O:31][CH3:32])[N:18]=[C:17]2[C:22]=1[N:23]=[C:24]([O:25][CH3:26])[N:16]2[CH2:15][CH2:14][CH:11]1[CH2:10][CH2:9][N:8]([CH2:6][C:42]2[CH:49]=[CH:48][C:45]([CH2:46][OH:47])=[CH:44][CH:43]=2)[CH2:13][CH2:12]1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acid2×HCID 11430Potassium CarbonateHCID 5107660[4-(Chloromethyl)phenyl]methanolHCID 592880219-(1-tert-Butoxycarbonylpiperidin-4-ylethyl)-8-methoxy-2-(2-methoxyethoxy)adenine

Product 1

HCID 59288029[4-(4-{2-[6-Amino-8-methoxy-2-(2-methoxyethoxy)purin-9-yl]ethyl}-piperidin-1-ylmethyl)phenyl]methanolYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To the compound (0.84 g, 1.86 mmol) obtained in Example 9, Step (i) was added trifluoroacetic acid (12 ml), and the mixture was stirred at room temperature for 20 minutes. Trifluoroacetic acid was evaporated by an evaporator, and DMF (15 ml), 4-(chloromethyl)benzyl alcohol (0.32 g, 2.04 mmol), and potassium carbonate (1.28 g, 9.30 mmol) were added thereto, and the mixture was stirred at room temperature for 18 hours. The carbonate was removed by filtration, and the filtrate was concentrated. Water was added to the residue, and the mixture was extracted three times with chloroform/ethanol=3/1. The resultant was dried over magnesium sulfate, concentrated, and purified by silica gel column (chloroform/methanol=20/1) to give the subtitle compound (0.52 g, 1.11 mmol) as a white solid. Yield: 60%.

Workup

  1. additionwere added
  2. stirringthe mixture was stirred at room temperature for 18 hours
  3. customThe carbonate was removed by filtration
  4. concentrationthe filtrate was concentrated
  5. additionWater was added to the residue
  6. extractionthe mixture was extracted three times with chloroform/ethanol=3/1
  7. dry with materialThe resultant was dried over magnesium sulfate
  8. concentrationconcentrated
  9. custompurified by silica gel column (chloroform/methanol=20/1)

Sources & evidence

ORD record
ord-a132641cf8c44031b01c341090b1a21e
Source dataset
uspto-grants-2011_10
Patent number
US08044056B2

Reaction notes

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