Tetrahydrofuran → HCID 58767047, compound

HRID 130309Notes

Reaction equation

HRID 130309 reaction equation
[CH3:1][Si:2]([CH3:55])([O:7][C@@H:8]1[C@H:12]([O:13][Si:14]([CH3:20])([CH3:19])[C:15]([CH3:18])([CH3:17])[CH3:16])[C@@H:11]([CH2:21][O:22][Si:23]([CH3:29])([CH3:28])[C:24]([CH3:27])([CH3:26])[CH3:25])[O:10][C@H:9]1[N:30]1[CH:38]=[N:37][C:36]2[C:31]1=[N:32][C:33]([N:45]1[CH:49]=[C:48]([C:50](OCC)=[O:51])[N:47]=[N:46]1)=[N:34][C:35]=2[NH:39][CH:40]1CC[CH2:42][CH2:41]1)[C:3]([CH3:6])([CH3:5])[CH3:4].[H-].[H-].[H-].[H-].[Li+].[Al+3].[NH4+].[Cl-].C1C[O:67][CH2:66]C1>>[CH3:1][Si:2]([CH3:55])([O:7][C@@H:8]1[C@H:21]([O:22][Si:23]([CH3:29])([CH3:28])[C:24]([CH3:25])([CH3:27])[CH3:26])[C@@H:11]([CH2:12][O:13][Si:14]([CH3:20])([CH3:19])[C:15]([CH3:16])([CH3:17])[CH3:18])[O:10][C@H:9]1[N:30]1[CH:38]=[N:37][C:36]2[C:31]1=[N:32][C:33]([N:45]1[CH:49]=[C:48]([CH2:50][OH:51])[N:47]=[N:46]1)=[N:34][C:35]=2[NH:39][CH:40]1[CH2:41][CH2:42][O:67][CH2:66]1)[C:3]([CH3:4])([CH3:5])[CH3:6]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 21226445Aluminium lithium hydrideHCID 58767044HCID 58767044, compound

Product 1

HCID 58767047HCID 58767047, compound

Conditions

Temperature
0 °C

Procedure

1.5 g of ethyl 1-(9-{(2R,3R,4R,5R)-3,4-bis(1,1,2,2-tetramethyl-1-silapropoxy)-5-[(1,1,2,2-tetramethyl-1-silapropoxy)methyl]oxolan-2-yl}-6-(cyclopentylamino)purin-2-yl)-1,2,3-triazole-4-carboxylate prepared as described in Example 9A is dissolved in 10 mL of THF and chilled in a 0° C. bath. 2 ml of LiAlH4 is added to this solution. The mixture is then allowed to warm to room temperature over a course of several hours. A saturated solution of NH4Cl is added dropwise to the room temperature solution until no bubbles are observed. The resulting precipitate may be filtered off and the filtrate concentrated down to remove all of the remaining solvent. The remaining aqueous solution is extracted with dichloromethane and the organic layer dried of MgSO4, filtered, and concentrated down to provide the product, [1-(9-{(2R,3R,4R,5R)-3,4-bis(1,1,2,2-tetramethyl-1-silapropoxy)-5-[(1,1,2,2-tetramethyl-1-silapropoxy)methyl]oxolan-2-yl}-6-(oxolan-3-ylamino)purin-2-yl)-1,2,3-triazole-4-yl]methan-1-ol, was purified by chromatography in a 5% methanol/dichloromethane solution.

Workup

  1. temperatureto warm to room temperature over a course of several hours
  2. filtrationThe resulting precipitate may be filtered off
  3. concentrationthe filtrate concentrated down
  4. customto remove all of the remaining solvent
  5. extractionThe remaining aqueous solution is extracted with dichloromethane
  6. dry with materialthe organic layer dried of MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated down

Sources & evidence

ORD record
ord-0d028ffb57c94e04aeb6e851cd251b76
Source dataset
uspto-grants-2008_06
Patent number
US07381714B2

Reaction notes

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