Ammonia → HCID 178508640, compound

HRID 1727326Notes

Reaction equation

HRID 1727326 reaction equation
C([O:8][CH2:9][CH2:10][C@@H:11]1[CH2:14][C@H:13]([N:15]2[CH:23]=[N:22][C:21]3[C:16]2=[N:17][CH:18]=[N:19][C:20]=3[NH2:24])[CH2:12]1)C1C=CC=CC=1.B(Cl)(Cl)Cl.N.CO>C(Cl)Cl>[OH:8][CH2:9][CH2:10][C@@H:11]1[CH2:14][C@H:13]([N:15]2[CH:23]=[N:22][C:21]3[C:16]2=[N:17][CH:18]=[N:19][C:20]=3[NH2:24])[CH2:12]1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 887MethanolHCID 25135Boron TrichlorideHCID 178508641HCID 178508641, compound

Product 1

HCID 178508640HCID 178508640, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

In a 10 mL flask with 9-[cis-3-(benzyloxyethyl)cyclobutyl]adenine (0.24 g, 0.74 mmol) inside, dry CH2Cl2 5 mL was added. After cooling to −78° C., BCl3 (1.0 M in CH2Cl2, 2.2 mL, 2.22 mmol) was added drop by drop. This was allowed to warm up to 0° C. and after 6 hr, the reaction was quenched by adding 7 N NH3 in MeOH (2.6 mL, 18.3 mmol) and the solvent was removed by rotovap. The crude material was applied directly to silica gel flash chromatography to give the desired product 0.1 g (58%). 1H NMR (CD3OD, 300 MHz): δ 1.75-1.84 (m, 2H), 2.27-2.44 (m, 3H), 2.71-2.80 (m, 2H), 3.56-3.62 (m, 2H), 4.82-4.95 (m, 1H), 8.22 (s, 1H), 8.30 (s, 1H). MS (FAB): expected for C11H15N5O (M+H)+ 234.27. Found 234.13489. IR (neat) νmax 3327, 3184, 2929, 1648, 1600, 1574, 1477, 1416, 1333, 1305, 1248, 1045, 798, 720, 648.

Workup

  1. temperatureto warm up to 0° C. and after 6 hr
  2. customthe reaction was quenched
  3. customthe solvent was removed by rotovap

Sources & evidence

ORD record
ord-b58ab31ec22145af9e5f5f560e204df5
Source dataset
uspto-grants-2009_02
Patent number
US07495006B2

Reaction notes

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