7-Chloro-2-iodothieno(3,2-b)pyridine → 5-(2,5-difluoro-4-(2-iodothieno[3,2-b]pyridin-7-yloxy)phenyl)-3-methyl-2-(phenylamino)pyrimidin-4(3H)-one

HRID 1676380Notes

Reaction equation

HRID 1676380 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([OH:8])[C:5]([F:9])=[CH:4][C:3]=1[C:10]1[C:11](=[O:24])[N:12]([CH3:23])[C:13]([NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[N:14][CH:15]=1.Cl[C:26]1[CH:31]=[CH:30][N:29]=[C:28]2[CH:32]=[C:33]([I:35])[S:34][C:27]=12>CN(C1C=CN=CC=1)C.BrC1C=CC=CC=1>[F:1][C:2]1[CH:7]=[C:6]([O:8][C:26]2[CH:31]=[CH:30][N:29]=[C:28]3[CH:32]=[C:33]([I:35])[S:34][C:27]=23)[C:5]([F:9])=[CH:4][C:3]=1[C:10]1[C:11](=[O:24])[N:12]([CH3:23])[C:13]([NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[N:14][CH:15]=1

Participants

5

Reactant 2

HCID 177504007-Chloro-2-iodothieno(3,2-b)pyridineHCID 673472775-(2,5-difluoro-4-hydroxyphenyl)-3-methyl-2-(phenylamino)pyrimidin-4(3H)-one

Product 1

HCID 673481795-(2,5-difluoro-4-(2-iodothieno[3,2-b]pyridin-7-yloxy)phenyl)-3-methyl-2-(phenylamino)pyrimidin-4(3H)-one

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 7961BromobenzeneSolvent

Procedure

A mixture of 5-(2,5-difluoro-4-hydroxyphenyl)-3-methyl-2-(phenylamino)pyrimidin-4(3H)-one (0.031 g, 0.093 mmol), 7-chloro-2-iodothieno[3,2-b]pyridine (0.025 g, 0.085 mmol; prepared according to the procedure of Ragan, J. A. Org. Proc. Res. 2003, 7, 676) and DMAP (0.010 g, 0.085 mmol) in bromobenzene (1.5 mL) under nitrogen was stirred at 150° C. for 6 days. The reaction was concentrated in vacuo to remove as much bromobenzene as possible and then purified directly by flash column chromatography, eluting with 20:1 CH2Cl2/MeOH. The product was obtained (10.5 mg; 21%) as a yellow solid. LRMS (APCI pos) m/e 589 (M+1).

Workup

  1. customprepared
  2. concentrationThe reaction was concentrated in vacuo
  3. customto remove as much bromobenzene as possible and
  4. customthen purified directly by flash column chromatography
  5. washeluting with 20:1 CH2Cl2/MeOH
  6. customThe product was obtained (10.5 mg; 21%) as a yellow solid

Sources & evidence

ORD record
ord-65a03d2f52804384ad161dcd2a80bd44
Source dataset
uspto-grants-2011_08
Patent number
US08003662B2

Reaction notes

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