Diisopropylethylamine → HCID 86643433, compound

HRID 1889597Notes

Reaction equation

HRID 1889597 reaction equation
[C@@H:1]1([N:9]2[C:18]3[N:17]=[CH:16][N:15]=[C:13]([OH:14])[C:12]=3[N:11]=[CH:10]2)[O:8][C@H:5]([CH2:6][OH:7])[C@@H:3]([OH:4])[CH2:2]1.F[P-](F)(F)(F)(F)F.[N:26]1(O[P+](N(C)C)(N(C)C)N(C)C)[C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=2[N:28]=[N:27]1.CCN(C(C)C)C(C)C>CN(C=O)C>[N:26]1([O:14][C:13]2[C:12]3[N:11]=[CH:10][N:9]([C:18]=3[N:17]=[CH:16][N:15]=2)[C@@H:1]2[O:8][C@H:5]([CH2:6][OH:7])[C@@H:3]([OH:4])[CH2:2]2)[C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=2[N:28]=[N:27]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 178521064HCID 178521064, compound

Product 1

HCID 86643433HCID 86643433, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a 50 mL round-bottomed flask equipped with a stirring bar were placed 2′-deoxyinosine 24 (0.504 g, 2.00 mmol) and BOP (1.770 g, 4.00 mmol). DMF (20 mL) and DIPEA (0.70 mL, 4.00 mmol) were added and the mixture was allowed to stir at room temperature for 26 h. The reaction mixture was evaporated with toluene several times. The crude product was dissolved in EtOAc and washed with water. The organic layer was separated, dried over Na2SO4 and concentrated. Chromatographic purification (SiO2, elution with 10% MeOH in CH2Cl2) afforded 0.421 g (57% yield) of compound 28 as a pale brownish-white foam. Rf (10% MeOH in CH2Cl2)=0.38. 1H NMR (500 MHz, CDCl3): δ 8.43 (s, 1H, Ar—H), 8.24 (s, 1H, Ar—H), 8.16-8.14 (m, 1H, Ar—H), 7.57-7.54 (m, 1H, Ar—H), 7.49-7.46 (m, 1H, Ar—H), 6.46 (dd, 1H, H-1′, J=9.2, 5.5), 5.10 (dd, 1H, OH, J=11.3, 2.3, CD3OD exchangeable), 4.83 (br m, 1H, H-3′), 4.25 (br s, 1H, H-4′), 3.97 (dt, 1H, H-5′, J=12.8, 2.0), 3.82 (app td, 1H, H-5′, Japp˜11.9, 1.8), 3.07 (ddd, 1H, H-2′, J=13.4, 9.5, 4.9), 2.42 (dd, 1H, H-2′, J=13.6, 5.7), 2.05 (d, 1H, OH, CD3OD exchangeable). 13C NMR (126 MHz, DMSO-d6): δ 159.1, 153.1, 151.1, 144.8, 143.2, 129.1, 128.8, 125.2, 120.5, 120.3, 108.7, 88.9, 86.9, 72.2, 62.7, 40.9. FAB HRMS calcd for C16H16N7O4 (M++H) 370.1264. found 370.1258.

Workup

  1. customIn a 50 mL round-bottomed flask equipped with a stirring bar
  2. customThe reaction mixture was evaporated with toluene several times
  3. dissolutionThe crude product was dissolved in EtOAc
  4. washwashed with water
  5. customThe organic layer was separated
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customChromatographic purification (SiO2, elution with 10% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-63a04c7567784989beccd16fda76213c
Source dataset
uspto-grants-2013_08
Patent number
US08501931B2

Reaction notes

Loading…