N,N-Dimethylaniline → 4-Chloro-2-(2-methoxyphenyl)thieno[3,2-d]pyrimidine

HRID 333702Notes

Reaction equation

HRID 333702 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[NH:10][C:11](=O)[C:12]2[S:17][CH:16]=[CH:15][C:13]=2[N:14]=1.O=P(Cl)(Cl)[Cl:21].CN(C)C1C=CC=CC=1.C([O-])(O)=O.[Na+]>C1C=CC=CC=1>[Cl:21][C:11]1[C:12]2[S:17][CH:16]=[CH:15][C:13]=2[N:14]=[C:9]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[O:2][CH3:1])[N:10]=1

Participants

6

Reactant 4

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychloride2×HCID 516892Sodium BicarbonateHCID 1359915042-(2-methoxyphenyl)thieno[3,2-d]pyrimidin-4(3H)-one

Product 1

HCID 590266334-Chloro-2-(2-methoxyphenyl)thieno[3,2-d]pyrimidineYield 71.1%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 2-(2-methoxyphenyl)thieno[3,2-d]pyrimidin-4(3H)-one (0.80 g, 3.1 mmol), POCl3 (0.28 mL, 3.1 mmol), and N,N-dimethylaniline (1.6 mL, 4.7 mmol) in benzene (3.5 mL) was heated at 80° C. for 2 h. An additional portion of POCl3 (0.28 mL, 3.1 mmol) was added, and the reaction was heated at 80° C. for 16 h. The reaction was cooled, and saturated aqueous NaHCO3 was slowly added. The organic layer was separated, washed with water, dried over Na2SO4, and concentrated under vacuum to give 4-chloro-2-(2-methoxyphenyl)thieno[3,2-d]pyrimidine (0.61 g, 71% yield). LC/MS: m/z 277.1 (M+H)+ at 2.98 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. temperatureThe reaction was cooled
  2. customThe organic layer was separated
  3. washwashed with water
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-37fd4a7dec204db6a8e96c41ff8176e4
Source dataset
uspto-grants-2014_11
Patent number
US08883781B2

Reaction notes

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