Trifluoroacetic acid → 6-[4-(Aminomethyl)phenyl]-N-(cyclopropylmethyl)-4-pyrimidinamine

HRID 1191101Notes

Reaction equation

HRID 1191101 reaction equation
[CH:1]1([CH2:4][NH:5][C:6]2[N:11]=[CH:10][N:9]=[C:8]([C:12]3[CH:26]=[CH:25][C:15]([CH2:16][NH:17]C(OC(C)(C)C)=O)=[CH:14][CH:13]=3)[CH:7]=2)[CH2:3][CH2:2]1.FC(F)(F)C(O)=O>C(Cl)Cl>[CH:1]1([CH2:4][NH:5][C:6]2[N:11]=[CH:10][N:9]=[C:8]([C:12]3[CH:13]=[CH:14][C:15]([CH2:16][NH2:17])=[CH:25][CH:26]=3)[CH:7]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58495648HCID 58495648, compound

Product 1

HCID 584956966-[4-(Aminomethyl)phenyl]-N-(cyclopropylmethyl)-4-pyrimidinamineYield 99.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve 4-[6-(cyclopropylmethyl-amino)-pyrimidin-4-yl]-N-(tert-butoxycarbonyl)-benzylamine (450 mg, 1.2 mmol) in DCM (5 mL). Add trifluoroacetic acid (3 mL) and stir under nitrogen for 3 h. Concentrate in vacuo and purify the crude mixture by SCX chromatography (5 g) to obtain the title compound (305 mg, 93%) suitable for use without additional purification. MS (ES+) m/z: 255 (M+H)+.

Workup

  1. concentrationConcentrate in vacuo
  2. custompurify the crude mixture by SCX chromatography (5 g)

Sources & evidence

ORD record
ord-251dbd4c39444aadad360e0441876d08
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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