Pyridine → 5'-Chloro-5'-deoxy-8-ethyladenosine

HRID 473564Notes

Reaction equation

HRID 473564 reaction equation
[Cl:1][CH2:2][C@H:3]1[O:7][C@@H:6]([N:8]2[C:17]3[N:16]=[CH:15][N:14]=[C:12]([NH2:13])[C:11]=3[N:10]=[C:9]2[CH3:18])[C@H:5]([OH:19])[C@@H:4]1[OH:20].N1C=CC=C[CH:22]=1.O=S(Cl)Cl>CC#N>[Cl:1][CH2:2][C@H:3]1[O:7][C@@H:6]([N:8]2[C:17]3[N:16]=[CH:15][N:14]=[C:12]([NH2:13])[C:11]=3[N:10]=[C:9]2[CH2:18][CH3:22])[C@H:5]([OH:19])[C@@H:4]1[OH:20]

Participants

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 251826935'-Chloro-5'-deoxy-8-methyladenosine

Product 1

HCID 251826945'-Chloro-5'-deoxy-8-ethyladenosine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The procedure was the same as reported above for 3a using 2b40 (1.28 g, 4.33 mmol), pyridine (685 mg, 0.70 mL, 8.65 mmol), CH3CN (10 mL), and SOCl2 (2.57 g, 1.58 mL, 21.60 mmol): yield 498 mg (37%); MS m/z 314 (M+H)+; 1HNMR (DMSO-d6) δ 8.09 (bs, 1H, H-2), 7.14 (bs, 2H, 6-NH2), 5.80 (d, 1H, H-1′, J1′,2′=5.7 Hz), 5.48 (d, 1H, 2′-OH, J2′-2′OH=6.1 Hz), 5.45 (d, 1H, 3′-OH, J3′-3′OH=5.4 Hz), 5.20 (ddd, 1H, H-2′, J1′,2′=5.7 Hz, J2′,3′=4.6 Hz, J2′-2′OH=6.1 Hz), 4.30-4.37 (bm, 1H, H-3′), 4.03-4.10 (bm, 1H, H-4′), 3.94-4.0 (m, 1H, 5′-CH2), 3.83-3.89 (m, 1H, 5′-CH2), 2.89 (q, 2H, 8-CH2CH3), 1.31 (t, 3H, 8-CH2CH3).

Sources & evidence

ORD record
ord-fab3166bf28d4ac096e40cb549d60c86
Source dataset
uspto-grants-2014_01
Patent number
US08637485B2

Reaction notes

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