Pentane → HCID 59975279, compound

HRID 2268397Notes

Reaction equation

HRID 2268397 reaction equation
Cl[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][N:3]=1.[NH2:10][CH2:11][C:12]1[N:20]=[C:19]2[C:15]([N:16]=[CH:17][N:18]2[C@H:21]2[C@H:25]([OH:26])[C@H:24]([OH:27])[C@@H:23]([CH2:28][O:29][CH3:30])[O:22]2)=[C:14]([NH:31][CH2:32][CH:33]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[N:13]=1.C(N(CC)CC)C.CCCCC>CN1CCCC1=O>[OH:26][C@@H:25]1[C@H:24]([OH:27])[C@@H:23]([CH2:28][O:29][CH3:30])[O:22][C@H:21]1[N:18]1[CH:17]=[N:16][C:15]2[C:19]1=[N:20][C:12]([CH2:11][NH:10][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][N:3]=1)=[N:13][C:14]=2[NH:31][CH2:32][CH:33]([C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

6

Reactant 4

HCID 8003PentaneHCID 8471TriethylamineHCID 51520946-Chloro-3-pyridinecarbonitrileHCID 9897827(2R,3R,4S,5R)-2-{2-(Aminomethyl)-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl}-5-(methoxymethyl)tetrahydro-3,4-furandiol

Product 1

HCID 59975279HCID 59975279, compoundYield 15.6%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
120 °C

Procedure

6-Chloronicotinonitrile (78 mg, 0.56 mmol) was added to a stirred solution of (2R,3R,4S,5R)-2-{2-(aminomethyl)-6-[(2,2-diphenylethyl)amino}-9H-purin-9-yl}-5-(methoxymethyl)tetrahydro-3,4-furandiol (250 mg, 0.51 mmol) (example 1) and triethylamine (57 mg, 0.56 mmol) in N-methyl-2-pyrrolidinone (10 ml). The reaction mixture was heated at 120° C. for 24 hr. The reaction mixture was then partitioned between water and ethyl acetate. The ethyl acetate layer was separated, washed with brine and dried with anhydrous magnesium sulfate. The solvent was removed under reduced pressure to give a residue that was purified by column chromatography on silica gel eluting with a solvent system of dichloromethane:methanol (95:5) to give material that was still impure and hence re-purified by column chromatography on silica gel eluting with a solvent system of ethyl acetate:methanol (90:10) to give a yellow oil which was treated with pentane to give the title compound (47 mg) as a solid. MS: 594 (MH+).

Workup

  1. customThe reaction mixture was then partitioned between water and ethyl acetate
  2. customThe ethyl acetate layer was separated
  3. washwashed with brine
  4. dry with materialdried with anhydrous magnesium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customto give a residue that
  7. customwas purified by column chromatography on silica gel eluting with a solvent system of dichloromethane:methanol (95:5)
  8. customto give material that
  9. customhence re-purified by column chromatography on silica gel eluting with a solvent system of ethyl acetate:methanol (90:10)
  10. customto give a yellow oil which

Sources & evidence

ORD record
ord-36a7dd81a8f7438c95cc873b8106f49f
Source dataset
uspto-grants-2001_12
Patent number
US06326359B1

Reaction notes

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