Hydrochloric Acid → HCID 22249265, compound

HRID 557374Notes

Reaction equation

HRID 557374 reaction equation
[CH3:1][S:2][C:3]1[N:8]=[C:7]([NH:9][CH2:10][C:11]2[CH:16]=[CH:15]C=[CH:13][CH:12]=2)[C:6]([C:17]([O:19]CC)=O)=[CH:5][N:4]=1.[OH-].[Na+].Cl.[CH:25]([C:28]1[CH:34]=[CH:33][C:31]([NH2:32])=[CH:30][CH:29]=1)([CH3:27])[CH3:26].C[N:36](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CCO.C(Cl)Cl>[CH:25]([C:28]1[CH:34]=[CH:33][C:31]([NH:32][C:17]([C:6]2[C:7]([NH:9][CH2:10][C:11]3[CH:12]=[CH:13][N:36]=[CH:15][CH:16]=3)=[N:8][C:3]([S:2][CH3:1])=[N:4][CH:5]=2)=[O:19])=[CH:30][CH:29]=1)([CH3:27])[CH3:26]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 74644-IsopropylanilineHCID 14798Sodium HydroxideHCID 295705ethyl 4-(benzylamino)-2-(methylthio)pyrimidine-5-carboxylateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 22249265HCID 22249265, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
45 °C

Procedure

To a solution of ethyl 2-methylthio-4-[benzylamino]-pyrimidine-5-carboxylate (0.1 g, 0.3 mmol, Step A) in EtOH (3 mL) was added 1 mL of aq. 1N NaOH solution. The resulting mixture was stirred at 45° C. for 2 h. The resulting mixture was neutralized with aq. 1N HCl and concentrated. To the residue in 3 mL of CH2Cl2 was added 4-isopropylaniline (90 mg, 0.66 mmol), HATU (0.18 g, 0.45 mmol), and 0.5 mL of TEA (0.36 g, 3.5 mmol). The resulting mixture was stirred at RT for 4 h and diluted with CH2Cl2. The organic solution was washed with H2O, dried over Na2SO4 and concentrated. The residue was purified by SiO2 chromatography to give N-[4-(isopropyl)phenyl]{2-methylthio-4-[(4-pyridylmethyl)amino]pyrimidin-5-yl}carboxamide. MS (ES+): 394 (M+H)+; (ES−): 392 (M−H)−. Calc'd C21H23N5OS−393.51.

Workup

  1. concentrationconcentrated
  2. stirringThe resulting mixture was stirred at RT for 4 h
  3. washThe organic solution was washed with H2O
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by SiO2 chromatography

Sources & evidence

ORD record
ord-b6a6b5eb4e3d4a8b8234392bc5eb53f5
Source dataset
uspto-grants-2011_11
Patent number
US08058445B2

Reaction notes

Loading…