Benzylamine → HCID 10259171, compound

HRID 1889612Notes

Reaction equation

HRID 1889612 reaction equation
N1(C2N=CN=C3C=2N=CN3[C@@H]2O[C@H](CO[Si](C(C)(C)C)(C)C)[C@@H](O[Si](C(C)(C)C)(C)C)C2)CCOCC1.N1(O[C:48]2[C:49]3[N:50]=[CH:51][N:52]([C:83]=3[N:84]=[CH:85][N:86]=2)[C@@H:53]2[O:82][C@H:72]([CH2:73][O:74][Si:75]([C:78]([CH3:81])([CH3:80])[CH3:79])([CH3:77])[CH3:76])[C@@H:63]([O:64][Si:65]([C:68]([CH3:71])([CH3:70])[CH3:69])([CH3:67])[CH3:66])[C@H:54]2[O:55][Si:56]([C:59]([CH3:62])([CH3:61])[CH3:60])([CH3:58])[CH3:57])C2C=CC=CC=2N=N1.[CH2:87]([NH2:94])[C:88]1[CH:93]=[CH:92][CH:91]=[CH:90][CH:89]=1.C([O-])([O-])=O.[Cs+].[Cs+]>COCCOC>[Si:56]([O:55][C@@H:54]1[C@H:73]([O:74][Si:75]([C:78]([CH3:79])([CH3:80])[CH3:81])([CH3:77])[CH3:76])[C@@H:72]([CH2:63][O:64][Si:65]([C:68]([CH3:71])([CH3:70])[CH3:69])([CH3:66])[CH3:67])[O:82][C@H:53]1[N:52]1[C:83]2[N:84]=[CH:85][N:86]=[C:48]([NH:94][CH2:87][C:88]3[CH:93]=[CH:92][CH:91]=[CH:90][CH:89]=3)[C:49]=2[N:50]=[CH:51]1)([C:59]([CH3:62])([CH3:60])[CH3:61])([CH3:57])[CH3:58]

Participants

6

Reactant 4

HCID 7504BenzylamineHCID 10796Cesium carbonateHCID 68468804HCID 68468804, compoundHCID 90879692HCID 90879692, compound

Product 1

HCID 10259171HCID 10259171, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

As described for the synthesis of 6-(morpholin-4-yl)-9-[2-deoxy-3,5-bis-O-(tert-butyldimethylsilyl)-β-D-erythro-pentofuranosyl]purine, this benzyl derivative was prepared by a reaction between O6-(benzotriazol-1-yl)-2′,3′,5′-tris-O-(tert-butyldimethylsilyl)inosine (27) (71.8 mg, 0.099 mmol) and benzylamine (21.8 μL, 0.200 mmol) in the presence of Cs2CO3 (65.2 mg, 0.200 mmol) in dry DME (1.0 mL) at room temperature over 7 h. Chromatographic purification (SiO2, elution with 3% EtOAc in hexanes followed by 20% EtOAc in hexanes) afforded 61.0 mg (87% yield) of the title compound as a clear gum. Rf (20% EtOAc in hexanes)=0.39. 1H NMR (500 MHz, CDCl3): δ 8.40 (s, 1H, Ar—H), 8.09 (s, 1H, Ar—H), 7.38 (d, 2H, Ar—H, J=7.3), 7.34 (t, 2H, Ar—H, J˜7.3), 7.28 (app t, 1H, Ar—H, Japp˜8.5), 6.02 (d, 1H, H-1′, J=5.4), 5.95 (br s, 1H, NH), 4.86 (br s, 2H, CH2), 4.70 (t, 1H, H-2′, J=4.9), 4.32 (t, 1H, H-3′, J=3.9), 4.12 (q, 1H, H-4′, J=3.4), 4.03 (dd, 1H, H-5′, J=11.2, 4.1), 3.78 (dd, 1H, H-5′, J=11.2, 2.9), 0.95, 0.93, 0.80 (3 s, 27H, tert-Bu), 0.13, 0.12, 0.11, 0.10, −0.04, −0.22 (6 s, 18H, SiCH3). 13C NMR (126 MHz, CDCl3): δ 154.7, 153.0, 149.4, 139.1, 138.6, 128.6, 127.7, 127.4, 120.4, 88.4, 85.4, 75.6, 72.1, 62.6, 44.8, 26.0, 25.8, 25.7, 18.4, 18.0, 17.8, −4.4, −4.7, −5.1, −5.4.

Workup

  1. customChromatographic purification (SiO2, elution with 3% EtOAc in hexanes followed by 20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-27eea4be0c3146b7914f4754c25a869f
Source dataset
uspto-grants-2013_08
Patent number
US08501931B2

Reaction notes

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