N,N-Dimethylaniline → 1624606-96-7

HRID 930440Notes

Reaction equation

HRID 930440 reaction equation
[F:1][CH:2]([F:13])[C:3]1[S:4][C:5]2[N:6]=[CH:7][N:8]=[C:9](O)[C:10]=2[N:11]=1.CN(C)C1C=CC=CC=1.P(Cl)(Cl)([Cl:25])=O>C1(C)C=CC=CC=1>[Cl:25][C:9]1[C:10]2[N:11]=[C:3]([CH:2]([F:13])[F:1])[S:4][C:5]=2[N:6]=[CH:7][N:8]=1

Participants

5

Reactant 3

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 178518072HCID 178518072, compound

Product 1

HCID 867322771624606-96-7

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-(difluoromethyl)thiazolo[5,4-d]pyrimidin-7-ol, N,N-dimethylaniline (0.800 mL, 6.31 mmol) and phosphorus oxychloride (6.00 mL, 65.5 mmol) in toluene (20 mL) was heated at 80° C. for 6 h. The reaction mixture was cooled of rt and the solvent removed invacuo. The residue was dissolved in DCM, evaporated onto silica gel and purified by flash chromatography (Isco (80 gram)) eluting with (EtOAc):hexanes (0:1→1:3) to give an off-white crystalline solid (252 mg, 18% over 2 steps). MS m/z=221.9, 223.9 [M+H]+. Calculated for C6H2F2N3S: 221.

Workup

  1. temperatureThe reaction mixture was cooled of rt
  2. customthe solvent removed invacuo
  3. dissolutionThe residue was dissolved in DCM
  4. customevaporated onto silica gel
  5. custompurified by flash chromatography (Isco (80 gram))
  6. washeluting with (EtOAc)
  7. customhexanes (0:1→1:3) to give an off-white crystalline solid (252 mg, 18% over 2 steps)

Sources & evidence

ORD record
ord-e75fe65d87614407ae8c605a5d82d42e
Source dataset
uspto-grants-2016_03
Patent number
US09296734B2

Reaction notes

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