(S)-4-(2-chloro-9-ethyl-8-iodo-9H-purin-6-yl)-3-methylmorpholine → (S)-4-(2-chloro-8-cyclopropyl-9-ethyl-9H-purin-6-yl)-3-methyl-morpholine

HRID 2063370Notes

Reaction equation

HRID 2063370 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7]([CH:12]3[CH2:14][CH2:13]3)[N:8]2[CH3:11])=[C:4]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][C@@H:16]2[CH3:21])[N:3]=1.Cl[C:23]1N=C2C(N=C(I)N2CC)=C(N2CCOC[C@@H]2C)N=1>>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7]([CH:12]3[CH2:13][CH2:14]3)[N:8]2[CH2:11][CH3:23])=[C:4]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][C@@H:16]2[CH3:21])[N:3]=1

Participants

3

Reactant 2

HCID 58222524(S)-4-(2-chloro-9-ethyl-8-iodo-9H-purin-6-yl)-3-methylmorpholineHCID 58222533(S)-4-(2-chloro-8-cyclopropyl-9-methyl-9H-purin-6-yl)-3-methylmorpholine

Product 1

HCID 58222534(S)-4-(2-chloro-8-cyclopropyl-9-ethyl-9H-purin-6-yl)-3-methyl-morpholine

Procedure

The compound (f-1) was prepared in an analogous fashion to (S)-4-(2-chloro-8-cyclopropyl-9-methyl-9H-purin-6-yl)-3-methylmorpholine, using (S)-4-(2-chloro-9-ethyl-8-iodo-9H-purin-6-yl)-3-methylmorpholine as the starting material. 1H NMR (CDCl3, 400 MHz) δ ppm 5.31 (broad s, 1H), 5.00 (broad s, 1H), 4.26 (q, J=7.2 Hz, 2H), 3.97 (dd, J=11.3, 3.4 Hz, 1H), 3.74 (m, 2H), 3.58 (td, J=12.2, 2.7, 1H), 3.43 (broad t, 1H), 1.92 (m, 1H), 1.41 (t, J=7.2 Hz, 3H), 1.34 (d, J=6.2 Hz, 3H), 1.12 (m, 2H), 1.06 (m, 2H); LC-MS m/z (method A)=322 [M+H]+, RT=2.81 min.

Sources & evidence

ORD record
ord-dd3aa29b4ea8496299a8ba075bea049e
Source dataset
uspto-grants-2012_10
Patent number
US08288381B2

Reaction notes

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