7-Chloro-2-iodothieno(3,2-b)pyridine → 2-(benzylamino)-5-(3-fluoro-4-(2-iodothieno[3,2-b]pyridin-7-yloxy)phenyl)-3-methylpyrimidin-4(3H)-one

HRID 1676385Notes

Reaction equation

HRID 1676385 reaction equation
[CH2:1]([NH:8][C:9]1[N:14]([CH3:15])[C:13](=[O:16])[C:12]([C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[C:19]([F:24])[CH:18]=2)=[CH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=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>[CH2:1]([NH:8][C:9]1[N:14]([CH3:15])[C:13](=[O:16])[C:12]([C:17]2[CH:22]=[CH:21][C:20]([O:23][C:26]3[CH:31]=[CH:30][N:29]=[C:28]4[CH:32]=[C:33]([I:35])[S:34][C:27]=34)=[C:19]([F:24])[CH:18]=2)=[CH:11][N:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 177504007-Chloro-2-iodothieno(3,2-b)pyridineHCID 673462122-(benzylamino)-5-(3-fluoro-4-hydroxyphenyl)-3-methylpyrimidin-4(3H)-one

Product 1

HCID 673487632-(benzylamino)-5-(3-fluoro-4-(2-iodothieno[3,2-b]pyridin-7-yloxy)phenyl)-3-methylpyrimidin-4(3H)-one

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 7961BromobenzeneSolvent

Procedure

A mixture of 2-(benzylamino)-5-(3-fluoro-4-hydroxyphenyl)-3-methylpyrimidin-4(3H)-one (0.036 g, 0.112 mmol), 7-chloro-2-iodothieno[3,2-b]pyridine (0.030 g, 0.102 mmol; prepared according to the procedure of Ragan, J. A. Org. Proc. Res. 2003, 7, 676) and DMAP (0.025 g, 0.20 mmol) in bromobenzene (1.5 mL) under nitrogen was stirred at 150° C. for 3 days. The reaction was concentrated in vacuo to remove as much bromobenzene as possible. MeOH was added to the residue and a brown solid precipitate was filtered and discarded. The filtrate was concentrated and then purified by flash column chromatography, eluting with 20:1 CH2Cl2/MeOH. The product was obtained (15.7 mg; 27%) as a yellow solid. LRMS (APCI pos) m/e 585 (M+1).

Workup

  1. customprepared
  2. concentrationThe reaction was concentrated in vacuo
  3. customto remove as much bromobenzene as possible
  4. additionMeOH was added to the residue
  5. filtrationa brown solid precipitate was filtered
  6. concentrationThe filtrate was concentrated
  7. custompurified by flash column chromatography
  8. washeluting with 20:1 CH2Cl2/MeOH
  9. customThe product was obtained (15.7 mg; 27%) as a yellow solid

Sources & evidence

ORD record
ord-fa6a58b906574bdd89f627f0cdce4cfb
Source dataset
uspto-grants-2011_08
Patent number
US08003662B2

Reaction notes

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