Ammonia → HCID 67388580, compound

HRID 905699Notes

Reaction equation

HRID 905699 reaction equation
CS([C:4]1[C:9]([C:10]([NH2:12])=[O:11])=[CH:8][N:7]=[C:6]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20][N+:21]3([O-])[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)=[CH:16][CH:15]=2)[N:5]=1)=O.[CH:28]([NH2:31])([CH3:30])[CH3:29].C(N(C(C)C)CC)(C)C.S([O-])(O)=O.[Na+].N>O.CC(N(C)C)=O>[O:24]1[CH2:25][CH2:26][N:21]([CH2:20][C:17]2[CH:18]=[CH:19][C:14]([NH:13][C:6]3[N:5]=[C:4]([NH:31][CH:28]([CH3:30])[CH3:29])[C:9]([C:10]([NH2:12])=[O:11])=[CH:8][N:7]=3)=[CH:15][CH:16]=2)[CH2:22][CH2:23]1

Participants

8

Reactant 5

HCID 222AmmoniaHCID 6363IsopropylamineHCID 81531DiisopropylethylamineHCID 23665763Sodium BisulfiteHCID 86602004HCID 86602004, compound

Product 1

HCID 67388580HCID 67388580, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 450 mg of 4-methylsulfinyl-2-({4-[(N-oxidomorpholin-4-yl)methyl]phenyl}amino)pyrimidine-5-carboxamide, 0.29 ml of isopropylamine, 0.24 ml of diisopropylethylamine and 5 ml of DMA was stirred at 80° C. for 3 hours. The reaction mixture was cooled down to room temperature, mixed with 8 ml of 5% sodium hydrogen sulfite, followed by stirring for 1 hour. The reaction mixture was adjusted to pH 9 by adding 0.5 ml of concentrated aqueous ammonia, diluted with water and then extracted with chloroform. The organic layer was washed with saturated brine, and then the solvent was evaporated. The resulting residue was purified by a silica gel column chromatography (chloroform:methanol:aqueous ammonia), and the resulting pale brown oil was crystallized from ethyl acetate to obtain 50 mg of 2-{[4-(morpholinomethyl)phenyl]amino}-4-(2-propylamino)pyrimidine-5-carboxamide as colorless crystals.

Workup

  1. temperatureThe reaction mixture was cooled down to room temperature
  2. stirringby stirring for 1 hour
  3. extractionextracted with chloroform
  4. washThe organic layer was washed with saturated brine
  5. customthe solvent was evaporated
  6. customThe resulting residue was purified by a silica gel column chromatography (chloroform:methanol:aqueous ammonia)
  7. customthe resulting pale brown oil was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-75a99fcd907c4cf8863244cb225345f5
Source dataset
uspto-grants-2011_09
Patent number
US08012959B2

Reaction notes

Loading…