Trifluoroacetic acid → N5-[5-(4-methoxy-phenyl)-pyrimidin-2-yl]-2-methyl-pyridine-3,5-diamine

HRID 2065571Notes

Reaction equation

HRID 2065571 reaction equation
C(OC(=O)[NH:7][C:8]1[C:9]([CH3:29])=[N:10][CH:11]=[C:12]([NH:14][C:15]2[N:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=3)=[CH:17][N:16]=2)[CH:13]=1)(C)(C)C.C(O)(C(F)(F)F)=O.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl.O>[CH3:28][O:27][C:24]1[CH:25]=[CH:26][C:21]([C:18]2[CH:17]=[N:16][C:15]([NH:14][C:12]3[CH:13]=[C:8]([NH2:7])[C:9]([CH3:29])=[N:10][CH:11]=3)=[N:20][CH:19]=2)=[CH:22][CH:23]=1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 67365563HCID 67365563, compound

Product 1

HCID 58171954N5-[5-(4-methoxy-phenyl)-pyrimidin-2-yl]-2-methyl-pyridine-3,5-diamine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

{5-[5-(4-Methoxy-phenyl)-pyrimidin-2-ylamino]-2-methyl-pyridin-3-yl}-carbamic acid tert-butyl ester 11 (0.33 mmol) is dissolved in DCM (2 mL) and treated with TFA (3 mL). The reaction mix is stirred at rt for 2 h. The solvent is removed to afford an off white solid residue. The residue is taken in water, the pH neutralized with 5% Na2CO3 and extracted with DCM:IPA=3:1 (3×40 mL). The organic layer is washed with brine and dried over Na2SO4. Evaporation of the organic solvent under reduced pressure affords N5-[5-(4-methoxy-phenyl)-pyrimidin-2-yl]-2-methyl-pyridine-3,5-diamine 12, which is used without further purification. 1H NMR (400 MHz, d6-DMSO) δ 10.37 (s, 1H), 8.90 (s, 2H), 8.47 (bs, 1H), 7.79 (bs, 1H), 7.71-7.69 (m, 2H), 7.08-7.06 (m, 2H), 6.36 (bs, 2H), 3.81 (s, 3H), 2.43 (s, 3H). MS (m/z) (M+1)+: 308.2.

Workup

  1. additionThe reaction mix
  2. customThe solvent is removed
  3. customto afford an off white solid residue
  4. extractionextracted with DCM
  5. washThe organic layer is washed with brine
  6. dry with materialdried over Na2SO4
  7. customEvaporation of the organic solvent under reduced pressure

Sources & evidence

ORD record
ord-1eb65d550ec14076bb95708fb62b09ec
Source dataset
uspto-grants-2012_10
Patent number
US08288540B2

Reaction notes

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