(+-)-2-Butanol → HCID 131717007, compound

HRID 728655Notes

Reaction equation

HRID 728655 reaction equation
[H-].[Na+].[NH2:3][C:4]1[N:12]=[C:11]2[C:7]([N:8]=[CH:9][N:10]2[C@@H:13]2[CH2:17][C@H:16]([CH2:18][OH:19])[CH:15]=[CH:14]2)=[C:6](Cl)[N:5]=1.[CH3:21][CH2:22][CH:23]([OH:25])[CH3:24]>>[NH2:3][C:4]1[N:12]=[C:11]2[C:7]([N:8]=[CH:9][N:10]2[C@@H:13]2[CH2:17][C@H:16]([CH2:18][OH:19])[CH:15]=[CH:14]2)=[C:6]([O:25][C@@H:23]([CH2:22][CH3:21])[CH3:24])[N:5]=1

Participants

4

Reactant 3

HCID 6568(+-)-2-ButanolHCID 24758Sodium hydrideHCID 4514744-(2-Amino-6-chloro-9H-purin-9-yl)-2-cyclopentene-1-methanol, (1S,4R)-

Product 1

HCID 131717007HCID 131717007, compound

Procedure

A flask was charged with sodium hydride (60% oil dispersion, 300 mg, 7.5 mmol) which was washed with hexanes before the addition of (±)-cis-4-(2-amino-6-chloro-9H--purin-9-yl)-2-cyclopentene-1-methanol from Example 4 (800 mg, 3 mmol) in ~10 mL of R-(-)-2-butanol. The solution was stirred at room temperature for 3 hours then at 60° C. (oil bath) for 1 hour. The solution was allowed to cool to room temperature before neutralization with 1 H HC1. The solution was concentrated and the residue chromatographed on silica gel. Title compound was eluted with 5% methanol-chloroform (0.81 g, 89%). Crystallization of such a sample from ethanol-acetonitrile yielded an off-white powder, m.p. 159-161° C.

Workup

  1. waitat 60° C. (oil bath) for 1 hour
  2. temperatureto cool to room temperature before neutralization with 1 H HC1
  3. concentrationThe solution was concentrated
  4. customthe residue chromatographed on silica gel
  5. washTitle compound was eluted with 5% methanol-chloroform (0.81 g, 89%)
  6. customCrystallization of such a sample from ethanol-acetonitrile
  7. customyielded an off-white powder, m.p. 159-161° C.

Sources & evidence

ORD record
ord-2e9f94216e73411591365ed42fd90884
Source dataset
uspto-grants-1991_09
Patent number
US05049671

Reaction notes

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