Dimethyl Sulfoxide → HCID 57756252, compound

HRID 911101Notes

Reaction equation

HRID 911101 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[C:9]([Cl:14])=[N:10][CH:11]=[CH:12][CH:13]=2)[CH:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].CS(C)=O.[O:25]1[CH2:30][CH2:29][N:28]([CH2:31][CH2:32][CH2:33][NH2:34])[CH2:27][CH2:26]1>CCOC(C)=O>[Cl:14][C:9]1[C:8]([C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH:34][CH2:33][CH2:32][CH2:31][N:28]3[CH2:29][CH2:30][O:25][CH2:26][CH2:27]3)[N:7]=2)=[CH:13][CH:12]=[CH:11][N:10]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 61055N-(3-Aminopropyl)morpholineHCID 249019302-Chloro-4-(2-chloropyridin-3-yl)pyrimidine

Product 1

HCID 57756252HCID 57756252, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To 2-chloro-4-(2-chloropyridin-3-yl)pyrimidine (100 mg, 0.44 mmol) and potassium carbonate (122 mg, 0.88 mmol) was added DMSO (1.0 mL) and 3-morpholinopropan-1-amine (77 mg, 0.53 mmol). The resulting mixture was heated for 15 hours at 80° C. The cooled reaction was diluted with EtOAc and extracted with water. The organic layer was dried over sodium sulfate, filtered and concentrated to yield the desired product as a yellow oil. MS m/z=334 [M+H]+. Calc'd for C16H20ClN5O: 333.84.

Workup

  1. customThe cooled reaction
  2. extractionextracted with water
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-6917e353f97540ff8abdf2f48a05baaa
Source dataset
uspto-grants-2011_09
Patent number
US08022221B2

Reaction notes

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