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

HRID 2063366Notes

Reaction equation

HRID 2063366 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7]([C:12]3([OH:18])[CH2:17]COCC3)[N:8]2[CH3:11])=[C:4]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][C@@H:20]2[CH3:25])[N:3]=1.[O:26]1CC(=O)[CH2:27]1>>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7]([C:12]3([OH:18])[CH2:17][O:26][CH2:27]3)[N:8]2[CH3:11])=[C:4]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][C@@H:20]2[CH3:25])[N:3]=1

Participants

3

Reactant 2

HCID 150242543-OxetanoneHCID 58222532(S)-4-(2-chloro-9-methyl-6-(3-methylmorpholino)-9H-purin-8-yl)tetrahydro-2H-pyran-4-ol

Product 1

HCID 58222531(S)-3-(2-chloro-9-methyl-6-(3-methylmorpholino)-9H-purin-8-yl)oxetan-3-ol

Procedure

This compound was prepared in an analogous fashion to (S)-4-(2-chloro-9-methyl-6-(3-methylmorpholino)-9H-purin-8-yl)tetrahydro-2H-pyran-4-ol, using 3-oxetanone as the starting material. 1H NMR (CDCl3, 400 MHz) δ ppm 5.35 (broad s, 2H), 5.15 (t, J=6.9 Hz, 2H), 4.96 (d, J=7.2 Hz, 2H), 4.00 (dd, J=11.2, 3 Hz, 1H), 3.84 (s, 3H), 3.81 to 3.71 (m, 2H), 3.59 (td, J=11.6, 2.7 Hz, 1H), 3.47 (broad s, 1H), 1.39 (d, J=6.8 Hz, 3H); LC-MS m/z (method B2)=340/342 [M+H]+, RT=1.59 min.

Sources & evidence

ORD record
ord-55c1215443cf4f468408bcfd45cbb587
Source dataset
uspto-grants-2012_10
Patent number
US08288381B2

Reaction notes

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