2,6-dichloro-9-ethyl-9H-purine → (S)-4-(2-chloro-9-ethyl-9H-purin-6-yl)-3-methylmorpholine

HRID 2063368Notes

Reaction equation

HRID 2063368 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH3:11])=[C:4]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][C@@H:13]2[CH3:18])[N:3]=1.Cl[C:20]1N=C2C(N=CN2CC)=C(Cl)N=1>>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:11][CH3:20])=[C:4]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][C@@H:13]2[CH3:18])[N:3]=1

Participants

3

Reactant 2

HCID 219883252,6-dichloro-9-ethyl-9H-purineHCID 58222544(S)-4-(2-chloro-9-methyl-9H-purin-6-yl)-3-methylmorpholine

Product 1

HCID 58222539(S)-4-(2-chloro-9-ethyl-9H-purin-6-yl)-3-methylmorpholine

Procedure

The compound (f-4) was prepared in an analogous fashion to (S)-4-(2-chloro-9-methyl-9H-purin-6-yl)-3-methylmorpholine, using 2,6-dichloro-9-ethyl-9H-purine as the starting material. 1H NMR (CDCl3, 400 MHz) δ ppm 7.71 (s, 1H), 5.41 (broad s, 1H), 5.00 (broad s, 1H), 4.19 (q, J=7.4 Hz, 2H), 4.00 (dd, J=7.8, 3.6 Hz, 1H), 3.76 (m, 2H), 3.61 (td, J=11.6, 2.6 Hz, 1H), 3.48 (broad s, 1H), 1.48 (t, J=7.2 Hz, 3H), 1.41 (d, J=6.8 Hz, 3H); LCMS m/z (method A)=284 [M+H]+, RT=2.06 min.

Sources & evidence

ORD record
ord-037e9e833e8a477f89b2744861633cb8
Source dataset
uspto-grants-2012_10
Patent number
US08288381B2

Reaction notes

Loading…