3-Oxetanone → (S)-3-(2-chloro-9-ethyl-6-(3-methylmorpholino)-9H-purin-8-yl)oxetan-3-ol

HRID 2063373Notes

Reaction equation

HRID 2063373 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7]([C:13]3([OH:19])[CH2:18]COCC3)[N:8]2[CH2:11][CH3:12])=[C:4]([N:20]2[CH2:25][CH2:24][O:23][CH2:22][C@@H:21]2[CH3:26])[N:3]=1.[O:27]1CC(=O)[CH2:28]1>>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7]([C:13]3([OH:19])[CH2:18][O:27][CH2:28]3)[N:8]2[CH2:11][CH3:12])=[C:4]([N:20]2[CH2:25][CH2:24][O:23][CH2:22][C@@H:21]2[CH3:26])[N:3]=1

Participants

3

Reactant 2

HCID 150242543-OxetanoneHCID 58222538(S)-4-(2-chloro-9-ethyl-6-(3-methylmorpholino)-9H-purin-8-yl)tetrahydro-2H-pyran-4-ol

Product 1

HCID 58222527(S)-3-(2-chloro-9-ethyl-6-(3-methylmorpholino)-9H-purin-8-yl)oxetan-3-ol

Procedure

This compound (i-j) was prepared in an analogous fashion to (S)-4-(2-chloro-9-ethyl-6-(3-methylmorpholino)-9H-purin-8-yl)tetrahydro-2H-pyran-4-ol, using 3-oxetanone as the starting material. 1H NMR (CDCl3, 500 MHz) δ ppm 5.70 to 4.70 (broad s, 2H), 5.20 (dd, J=12.1 Hz, 7.2 Hz, 2H), 4.95 (d, J=7.2 Hz, 2H), 4.31 (q, J=7.1 Hz, 2H), 4.02 (dd, J=11.3, 3.2 Hz, 1H), 3.78 (dt, J=11.7 Hz, 7.2 Hz, 2H), 3.61 (td, J=11.9 Hz, 2.7 Hz, 1H), 3.47 (s, 2H), 1.46 (t, J=7.2 Hz, 3H), 1.41 (d, J=6.8 Hz, 3H); LC-MS m/z (method B2)=354/356 [M+H]+, RT=1.71 min.

Sources & evidence

ORD record
ord-abbc952ac2fe4c64874a4a3c127e8322
Source dataset
uspto-grants-2012_10
Patent number
US08288381B2

Reaction notes

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