tert-butyl 3-(6-[N-methyl-N-phenylamino]pyrimidin-4-ylamino)phenylcarbamate → 3-[6-(N-methyl-N-phenylamino)-pyrimidin-4-ylamino]phenylamine

HRID 1053190Notes

Reaction equation

HRID 1053190 reaction equation
[CH3:1][N:2]([C:9]1[N:14]=[CH:13][N:12]=[C:11]([NH:15][C:16]2[CH:17]=[C:18]([NH:22]C(=O)OC(C)(C)C)[CH:19]=[CH:20][CH:21]=2)[CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>C(O)(C(F)(F)F)=O>[CH3:1][N:2]([C:9]1[N:14]=[CH:13][N:12]=[C:11]([NH:15][C:16]2[CH:17]=[C:18]([NH2:22])[CH:19]=[CH:20][CH:21]=2)[CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

3

Reactant 1

HCID 66769589tert-butyl 3-(6-[N-methyl-N-phenylamino]pyrimidin-4-ylamino)phenylcarbamate

Product 1

HCID 577083423-[6-(N-methyl-N-phenylamino)-pyrimidin-4-ylamino]phenylamineYield 75%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of tert-butyl 3-(6-[N-methyl-N-phenylamino]pyrimidin-4-ylamino)phenylcarbamate (1.17 g, 3 mmol) and TFA (50% in DCM, 10 mL) was stirred at RT for 4 hr. The reaction solvent was removed under vacuum. The crude product was mixed with 1 mL of 2N NaOH and 5 mL of EtOAc, was stirred for 30 min, was filtered, and was dried under vacuum to give 0.65 g (75%) of the title compound, an off-white solid. (IR-8) MS (m/z): MH+=292.

Workup

  1. customThe reaction solvent was removed under vacuum
  2. additionThe crude product was mixed with 1 mL of 2N NaOH and 5 mL of EtOAc
  3. stirringwas stirred for 30 min
  4. filtrationwas filtered
  5. customwas dried under vacuum

Sources & evidence

ORD record
ord-ce19397d3d6449b6b07f1a1fd7adf64a
Source dataset
uspto-grants-2016_07
Patent number
US09393246B2

Reaction notes

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