2-Fluoro-4-nitrophenol → 4-(3-Chloro-4-nitrophenoxy)thieno[3,2-d]pyrimidine

HRID 500826Notes

Reaction equation

HRID 500826 reaction equation
Cl[C:2]1[C:3]2[S:10][CH:9]=[CH:8][C:4]=2[N:5]=[CH:6][N:7]=1.FC1C=C([N+]([O-])=O)C=CC=1OC1C2SC(C(NCCN3CCOCC3)=O)=CC=2N=CN=1.FC1C=C([N+]([O-])=O)C=CC=1O.[Cl:53][C:54]1[CH:55]=[C:56]([OH:63])[CH:57]=[CH:58][C:59]=1[N+:60]([O-:62])=[O:61]>>[Cl:53][C:54]1[CH:55]=[C:56]([CH:57]=[CH:58][C:59]=1[N+:60]([O-:62])=[O:61])[O:63][C:2]1[C:3]2[S:10][CH:9]=[CH:8][C:4]=2[N:5]=[CH:6][N:7]=1

Participants

5

Reactant 4

HCID 98252-Fluoro-4-nitrophenolHCID 102833-Chloro-4-nitrophenolHCID 27358214-Chlorothieno[3,2-d]pyrimidineHCID 594245534-(2-Fluoro-4-nitrophenoxy)-N-(2-morpholinoethyl)thieno[3,2-d]pyrimidine-6-carboxamide

Product 1

HCID 474463624-(3-Chloro-4-nitrophenoxy)thieno[3,2-d]pyrimidineYield 72%

Procedure

Starting from the chloride 20 (scheme 4) and following the procedure described above for the synthesis of compound 24 (scheme 4, example 22) remplacing 2-fluoro-4-nitrophenol with 3-chloro-4-nitrophenol, title compound 171 was obtained in 72% yield. LRMS (M+1) 307.7 (100%).

Sources & evidence

ORD record
ord-5512f104ab1a4b8dbb0cca2b407814ff
Source dataset
uspto-grants-2010_08
Patent number
US07772247B2

Reaction notes

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