Ammonium Chloride → HCID 10322053, compound

HRID 720629Notes

Reaction equation

HRID 720629 reaction equation
[Na].[CH2:2]([N:6]1[C:14]2[N:13]=[C:12]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([NH:22][C:23](=[O:25])[CH3:24])=[CH:18][CH:17]=3)[NH:11][C:10]=2[C:9](=[O:26])[N:8]([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[O:34][Si](C(C)(C)C)(C)C)[C:7]1=[O:42])[CH2:3][CH2:4][CH3:5].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Cl-].[NH4+]>O1CCCC1.C(OCC)(=O)C>[CH2:2]([N:6]1[C:14]2[N:13]=[C:12]([CH2:15][C:16]3[CH:17]=[CH:18][C:19]([NH:22][C:23](=[O:25])[CH3:24])=[CH:20][CH:21]=3)[NH:11][C:10]=2[C:9](=[O:26])[N:8]([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[OH:34])[C:7]1=[O:42])[CH2:3][CH2:4][CH3:5]

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 68863790HCID 68863790, compound

Product 1

HCID 10322053HCID 10322053, compoundYield 20.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of N-(4-{3-butyl-1-[2-(tert-butyl-dimethyl-silanyloxy)-benzyl]-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-ylmethyl}-phenyl)-acetamide sodium salt (75 mg, 0.12 mmol) in tetrahydrofuran cooled to 0° C. was treated with tetrabutylammonium fluoride. The reaction was stirred at 0° C. for 1.5 h. At this time, the reaction mixture was treated with a saturated aqueous ammonium chloride solution (1.0 mL) and then diluted with ethyl acetate (50 mL). This solution was washed with water and brine. The organics were dried over magnesium sulfate, filtered, and concentrated in vacuo. The resulting residue was diluted with acetonitrile. The insolubles were collected, washed with acetonitrile, and dried in vacuo for 24 hrs to afford N-{4-[3-butyl-1-(2-hydroxy-benzyl)-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-ylmethyl]-phenyl}-acetamide (11.4 mg, 19%) as a white solid: EI-HRMS m/e calcd for C25H27N5O4 (M+) 461.2063, found 461.2073.

Workup

  1. washThis solution was washed with water and brine
  2. dry with materialThe organics were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. additionThe resulting residue was diluted with acetonitrile
  6. customThe insolubles were collected
  7. washwashed with acetonitrile
  8. customdried in vacuo for 24 hrs

Sources & evidence

ORD record
ord-14f5491342884d38b80cf3cdb90fc23f
Source dataset
uspto-grants-2006_11
Patent number
US07135475B2

Reaction notes

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