Hydrochloric Acid → n2-[4-(Dimethylphosphoryl)-2-methoxyphenyl]-n4-[2-(propan-2-ylsulfonyl)phenyl]pyrimidine-2,4-diamine

HRID 1471965Notes

Reaction equation

HRID 1471965 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[S:15]([CH:18]([CH3:20])[CH3:19])(=[O:17])=[O:16])[CH:5]=[CH:4][N:3]=1.[CH3:21][P:22]([C:25]1[CH:31]=[CH:30][C:28]([NH2:29])=[C:27]([O:32][CH3:33])[CH:26]=1)([CH3:24])=[O:23].Cl>COCCO>[CH3:24][P:22]([C:25]1[CH:31]=[CH:30][C:28]([NH:29][C:2]2[N:7]=[C:6]([NH:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[S:15]([CH:18]([CH3:20])[CH3:19])(=[O:17])=[O:16])[CH:5]=[CH:4][N:3]=2)=[C:27]([O:32][CH3:33])[CH:26]=1)([CH3:21])=[O:23]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 67052699(4-Amino-3-methoxyphenyl)dimethylphosphine oxideHCID 866687912-Chloro-N-(2-(isopropylsulfonyl)phenyl)pyrimidin-4-amine

Product 1

HCID 68165220n2-[4-(Dimethylphosphoryl)-2-methoxyphenyl]-n4-[2-(propan-2-ylsulfonyl)phenyl]pyrimidine-2,4-diamineYield 72%

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 2-chloro-N-[2-(propan-2-ylsulfonyl)phenyl]-pyrimidin-4-amine (0.017 g, 0.054 mmol) in 0.5 mL of 2-methoxyethanol in a vial was added 4-(dimethylphosphoryl)-2-methyoxyaniline (0.010 g, 0.044 mmol) as the HCl salt. The vial was sealed and the reaction was heated at 90° C. for 16 h. The reaction was quenched with 1N NaOH solution and the solution extracted ethyl acetate. The organic layers were combined, washed with saturated sodium chloride solution, dried with sodium sulfate, filtered and concentrated. The crude residue was purified by silica gel chromatography (0-10% 7N ammonia in methanol:dichloromethane) to afford the desired compound (15 mg, 72% yield). MS/ES+: m/z=475.

Workup

  1. customThe vial was sealed
  2. customThe reaction was quenched with 1N NaOH solution
  3. extractionthe solution extracted ethyl acetate
  4. washwashed with saturated sodium chloride solution
  5. dry with materialdried with sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude residue was purified by silica gel chromatography (0-10% 7N ammonia in methanol:dichloromethane)

Sources & evidence

ORD record
ord-c44cb79468c7423e98d1cc9f1917dca3
Source dataset
uspto-grants-2015_04
Patent number
US09012462B2

Reaction notes

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