N,N-Dimethylaniline → HCID 59026627, compound

HRID 333711Notes

Reaction equation

HRID 333711 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[C:17]([CH3:18])=[CH:16][S:15][C:13]=2[N:14]=1.O=P(Cl)(Cl)[Cl:22].CN(C)C1C=CC=CC=1.C([O-])(O)=O.[Na+]>C1C=CC=CC=1>[Cl:22][C:11]1[C:12]2[C:17]([CH3:18])=[CH:16][S: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 oxychlorideHCID 516892Sodium BicarbonateHCID 59026635HCID 59026635, compound

Product 1

HCID 59026627HCID 59026627, compoundYield 91.7%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 2-(2-methoxyphenyl)-5-methylthieno[2,3-d]pyrimidin-4(3H)-one (0.4 g, 1.5 mmol), POCl3 (0.14 mL, 1.5 mmol), and N,N-dimethylaniline (0.29 mL, 2.25 mmol) in benzene (1.7 mL) was heated at 80° C. for 2 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)-5-methylthieno[2,3-d]pyrimidine (0.4 g, 91% yield). LC/MS: m/z 291.1 (M+H)+ at 3.31 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-cb5ab3f1204c4ba69f5651b3c6e2e439
Source dataset
uspto-grants-2014_11
Patent number
US08883781B2

Reaction notes

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