(S)-4-(2-chloro-8-(3-fluorooxetan-3-yl)-9-methyl-9H-pur-in-6-yl)-3-methylmorpholine → (S)-4-(2-chloro-9-ethyl-8-(4-fluorotetrahydro-2H-pyran-4-yl)-9H-purin-6-yl)-3-methylmorpholine

HRID 2063372Notes

Reaction equation

HRID 2063372 reaction equation
ClC1N=C2C(N=C(C3([F:16])COC3)N2C)=C(N2CCOC[C@@H]2C)N=1.[Cl:24][C:25]1[N:33]=[C:32]2[C:28]([N:29]=[C:30]([C:36]3(O)[CH2:41][CH2:40][O:39][CH2:38][CH2:37]3)[N:31]2[CH2:34][CH3:35])=[C:27]([N:43]2[CH2:48][CH2:47][O:46][CH2:45][C@@H:44]2[CH3:49])[N:26]=1>>[Cl:24][C:25]1[N:33]=[C:32]2[C:28]([N:29]=[C:30]([C:36]3([F:16])[CH2:41][CH2:40][O:39][CH2:38][CH2:37]3)[N:31]2[CH2:34][CH3:35])=[C:27]([N:43]2[CH2:48][CH2:47][O:46][CH2:45][C@@H:44]2[CH3:49])[N:26]=1

Participants

3

Reactant 2

HCID 58222529(S)-4-(2-chloro-8-(3-fluorooxetan-3-yl)-9-methyl-9H-pur-in-6-yl)-3-methylmorpholineHCID 58222538(S)-4-(2-chloro-9-ethyl-6-(3-methylmorpholino)-9H-purin-8-yl)tetrahydro-2H-pyran-4-ol

Product 1

HCID 58222520(S)-4-(2-chloro-9-ethyl-8-(4-fluorotetrahydro-2H-pyran-4-yl)-9H-purin-6-yl)-3-methylmorpholine

Procedure

This compound (h-1) was prepared in an analogous fashion to (S)-4-(2-chloro-8-(3-fluorooxetan-3-yl)-9-methyl-9H-pur-in-6-yl)-3-methylmorpholine, using (S)-4-(2-chloro-9-ethyl-6-(3-methylmorpholino)-9H-purin-8-yl)tetrahydro-2H-pyran-4-ol as the starting material. 1H NMR (CDCl3, 500 MHz) δ ppm 5.90 to 4.60 (broad s, 2H), 4.37 (q, J=7.1 Hz, 2H), 4.02 (dd, J=11.4 Hz, 3.4 Hz, 1H), 3.98 to 3.86 (m, 4H), 3.78 (dt, J=11.7 Hz, 7.1 Hz, 2H), 3.62 (td, J=11.9 Hz, 2.8 Hz, 1H), 3.48 (d, J=7.0 Hz, 1H), 2.55 to 2.35 (m, 2H), 2.22 to 2.06 (m, 2H), 1.43 (t, J=7.1 Hz, 3H), 1.40 (d, J=6.8 Hz, 3H); LC-MS m/z (method B2)=384 [M+H]+, RT=2.10 min.

Sources & evidence

ORD record
ord-c3080594278a43e2a20bda45f628ad15
Source dataset
uspto-grants-2012_10
Patent number
US08288381B2

Reaction notes

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