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

HRID 1711055Notes

Reaction equation

HRID 1711055 reaction equation
[F:1][C:2]1[CH:20]=[C:19]([N+:21]([O-])=O)[CH:18]=[CH:17][C:3]=1[O:4][C:5]1[C:6]2[S:13][C:12]([S:14]([CH3:16])=[O:15])=[CH:11][C:7]=2[N:8]=[CH:9][N:10]=1.FC1C=C(N[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])C=CC=1OC1C2SC(SC)=CC=2N=CN=1>>[F:1][C:2]1[CH:20]=[C:19]([NH:21][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:18]=[CH:17][C:3]=1[O:4][C:5]1[C:6]2[S:13][C:12]([S:14]([CH3:16])=[O:15])=[CH:11][C:7]=2[N:8]=[CH:9][N:10]=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 59424630N-(3-Fluoro-4-(6-(methylsulfinyl)thieno[3,2-d]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-5d14b8c98b76403abd9b4e95263b886b
Source dataset
uspto-grants-2010_09
Patent number
US07790729B2

Reaction notes

Loading…