4-(2-Fluoro-4-nitrophenoxy)-6-(methylsulfinyl)thieno[3,2-d]pyrimidine → N-(3-Fluoro-4-(6-(methylsulfinyl)thieno[3,2-]pyrimidin-4-yloxy)phenyl carbamothioyl)-2-phenylacetamide

HRID 1261350Notes

Reaction equation

HRID 1261350 reaction equation
FC1C=C([N+]([O-])=O)C=CC=1OC1[C:6]2[S:13][C:12]([S:14]([CH3:16])=[O:15])=[CH:11][C:7]=2N=CN=1.[F:24][C:25]1[CH:26]=[C:27]([NH:43][C:44]([NH:46][C:47](=[O:55])[CH2:48][C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)=[S:45])[CH:28]=[CH:29][C:30]=1[O:31][C:32]1C2SC(SC)=CC=2[N:35]=[CH:36][N:37]=1>>[F:24][C:25]1[CH:26]=[C:27]([NH:43][C:44]([NH:46][C:47](=[O:55])[CH2:48][C:49]2[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=2)=[S:45])[CH:28]=[CH:29][C:30]=1[O:31][C:32]1[C:7]2[CH:11]=[C:12]([S:14]([CH3:16])=[O:15])[S:13][C:6]=2[N:35]=[CH:36][N:37]=1

Participants

3

Reactant 2

HCID 594245544-(2-Fluoro-4-nitrophenoxy)-6-(methylsulfinyl)thieno[3,2-d]pyrimidineHCID 59424579N-(3-Fluoro-4-(6-(methylthio)thieno[3,2-d]pyrimidin-4-yloxy)phenylcarbamothioyl)-2-phenylacetamide

Product 1

HCID 86644589N-(3-Fluoro-4-(6-(methylsulfinyl)thieno[3,2-]pyrimidin-4-yloxy)phenyl carbamothioyl)-2-phenylacetamideYield 36%

Procedure

Starting from the compound 285 and following the procedure described above for the synthesis of compound 283 (scheme 64, step 4, example 225), title compound 286 was obtained in 36% yield as an off-white solid. 1H NMR (DMSO-d6) δ (ppm): 12.45(s, 1H), 11.83(s, 1H), 8.80(s, 1H), 8.13(s, 1H), 7.93(dd, 1H, J1=2.3 Hz, J2=10.9 Hz), 7.55 (t, 1H, J=8.6 Hz), 7.48 (m, 1H), 7.34-7.31(m, 4H), 7.28-7.25(m, 1H), 3.81(s, 2H), 3.08(s, 3H). MS (m/z): 501.0(M+H) (found).

Sources & evidence

ORD record
ord-83e91753653841f2a4d3ec17950d44d4
Source dataset
uspto-grants-2013_06
Patent number
US08470850B2

Reaction notes

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