Dimethylformamide → 2-(1-Benzothien-2-yl)-4-chloropyrido[2,3-d]pyrimidine

HRID 1992313Notes

Reaction equation

HRID 1992313 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]1[N:11]=[C:12](O)[C:13]2[CH:19]=[CH:18][CH:17]=[N:16][C:14]=2[N:15]=1.S(Cl)([Cl:23])=O.CN(C=O)C>C(Cl)(Cl)Cl>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]1[N:11]=[C:12]([Cl:23])[C:13]2[CH:19]=[CH:18][CH:17]=[N:16][C:14]=2[N:15]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 178517407HCID 178517407, compound

Product 1

HCID 591303752-(1-Benzothien-2-yl)-4-chloropyrido[2,3-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a suspension of 2-(1-benzothien-2-yl)pyrido[2,3-d]pyrimidin-4-ol (150 mg, 0.54 mmol) in chloroform (10 mL) was added thionyl chloride (0.47 mL, 6.4 mmol) and a catalytic amount of DMF. The reaction was heated to reflux for 4 h and allowed to cool to rt. The solvent was removed under reduced pressure and the resultant product was (18.2 mg, 12%) used directly in the next step without further purification. HPLC/MS: (M+H)+ 298.2 m/z; Retention time (LC-MS)=3.76 min; 1H NMR (DMSO)-D6): 9.24(1H, m); 8.73(1H, d); 8.55(1H, s); 8.10(2H, t); 7.86(1H, m); 7.50(2H, m).

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 4 h
  3. customThe solvent was removed under reduced pressure
  4. customused directly in the next step without further purification

Sources & evidence

ORD record
ord-e2847f7e202f4fd2b897c026d406c871
Source dataset
uspto-grants-2010_01
Patent number
US07648986B2

Reaction notes

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