Tert-Butylamine → HCID 9817873, compound

HRID 728658Notes

Reaction equation

HRID 728658 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@@H:11]2[CH2:15][C@H:14]([CH2:16][OH:17])[CH:13]=[CH:12]2)=[C:4](Cl)[N:3]=1.[C:19]([NH2:23])([CH3:22])([CH3:21])[CH3:20]>>[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@@H:11]2[CH2:15][C@H:14]([CH2:16][OH:17])[CH:13]=[CH:12]2)=[C:4]([NH:23][C:19]([CH3:22])([CH3:21])[CH3:20])[N:3]=1

Participants

3

Reactant 2

HCID 6385Tert-ButylamineHCID 4514744-(2-Amino-6-chloro-9H-purin-9-yl)-2-cyclopentene-1-methanol, (1S,4R)-

Product 1

HCID 9817873HCID 9817873, compoundYield 65%

Procedure

(±)-cis-4-(2-Amino-6-chloro-9H-purin-9-yl)-2-cyclopentene-1-methanol from Example 4 (0.544 g, 2.0 mmol) and tert-butylamine (15 mL) were heated at 80° C. in a Parr bomb for 28 hours. The resulting solution was concentrated and the residual oil was dried by evaporation of ethanol and chromatographed on silica gel. Title compound was eluted with 5% methanol-chloroform; crystallization from acetonitrile gave white powder (0.392 g, 65%), m.p. 161-163° C.

Workup

  1. concentrationThe resulting solution was concentrated
  2. dry with materialthe residual oil was dried by evaporation of ethanol
  3. customchromatographed on silica gel
  4. washTitle compound was eluted with 5% methanol-chloroform
  5. customcrystallization from acetonitrile

Sources & evidence

ORD record
ord-f815b86cf11742beb237705ef84a0340
Source dataset
uspto-grants-1991_09
Patent number
US05049671

Reaction notes

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