Trifluoroacetic acid → N-(4-(methoxymethyl)-2-nitrophenyl)-N6-methylpyrimidine-4,6-diamine

HRID 58186Notes

Reaction equation

HRID 58186 reaction equation
C(O)(C(F)(F)F)=O.C(OC([N:15]([C:31]1[CH:36]=[CH:35][C:34]([CH2:37][O:38][CH3:39])=[CH:33][C:32]=1[N+:40]([O-:42])=[O:41])[C:16]1[N:21]=[CH:20][N:19]=[C:18]([N:22](C)[C:23](=O)OC(C)(C)C)[CH:17]=1)=O)(C)(C)C>C(Cl)Cl>[CH3:39][O:38][CH2:37][C:34]1[CH:35]=[CH:36][C:31]([NH:15][C:16]2[CH:17]=[C:18]([NH:22][CH3:23])[N:19]=[CH:20][N:21]=2)=[C:32]([N+:40]([O-:42])=[O:41])[CH:33]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131736982HCID 131736982, compound

Product 1

HCID 118028374N-(4-(methoxymethyl)-2-nitrophenyl)-N6-methylpyrimidine-4,6-diamineYield 139.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (5 mL) was slowly added to a stirred solution of tert-butyl (6-((tert-butoxycarbonyl)(4-(methoxymethyl)-2-nitrophenyl)amino)pyrimidin-4-yl)(methyl)carbamate (0.85 g) in dry DCM (10 mL) under argon atmosphere at 0° C. The resulting reaction mixture was allowed to warm to room temperature and stirred for 1 h. After completion of the reaction, excess solvents were removed under reduced pressure and washed with ether to afford the title compound (0.7 g crude) as a solid. MS (ESI): 290.2 [M+H]+.

Workup

  1. customThe resulting reaction mixture
  2. customAfter completion of the reaction, excess solvents
  3. customwere removed under reduced pressure
  4. washwashed with ether

Sources & evidence

ORD record
ord-c3bd7fee5bc4406296130b56b00336bd
Source dataset
uspto-grants-2016_09
Patent number
US09434697B2

Reaction notes

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