N,N-Dimethylaniline → 5,7-Dichloro-2-methylthiazolo[5,4-d]pyrimidine

HRID 1919351Notes

Reaction equation

HRID 1919351 reaction equation
[CH3:1][C:2]1[S:3][C:4]2[NH:5][C:6](=O)[NH:7]C(=O)[C:9]=2[N:10]=1.CN(C)C1C=CC=CC=1.P(Cl)(Cl)([Cl:24])=O.[CH2:27]([Cl:29])Cl>>[Cl:24][C:6]1[N:7]=[C:27]([Cl:29])[C:9]2[N:10]=[C:2]([CH3:1])[S:3][C:4]=2[N:5]=1

Participants

5

Reactant 4

HCID 949N,N-DimethylanilineHCID 6344DichloromethaneHCID 24813Phosphorus oxychlorideHCID 3456422-methyl-4H-thiazolo[5,4-d]pyrimidine-5,7-dione

Product 1

HCID 3456395,7-Dichloro-2-methylthiazolo[5,4-d]pyrimidineYield 54%

Conditions

Temperature
130 °C

Procedure

To a mixture of 2-methyl-4H-thiazolo[5,4-d]pyrimidine-5,7-dione (7.5 g, 0.041 mol) in N,N-dimethylaniline (3.7 mL, 0.029 mol) was added phosphorous oxychloride (38.0 mL, 0.410 mol) and the mixture heated at 130° C. for 4 h. The resulting black solution was cooled to RT, then carefully quenched with crushed ice and H2O, before being extracted with EtOAc. The organic layer was isolated, dried (MgSO4) and concentrated in vacuo to give a yellow solid. The solid was dissolved in DCM, then washed with an aqueous solution of NaHCO3 followed by brine, dried (Na2SO4) and concentrated in vacuo to give the title compound as a pale yellow solid (4.90 g, 54%).

Workup

  1. temperatureThe resulting black solution was cooled to RT
  2. customcarefully quenched with crushed ice and H2O
  3. extractionbefore being extracted with EtOAc
  4. customThe organic layer was isolated
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customto give a yellow solid
  8. washwashed with an aqueous solution of NaHCO3
  9. dry with materialdried (Na2SO4)
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7a1968a1fdf74428bcb6c6770a87d47b
Source dataset
uspto-grants-2012_05
Patent number
US08168633B2

Reaction notes

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