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Trifluoroacetic acid → 4-[4-(Cyclopropylmethyl-amino)-pyrimidin-2-yl]-benzylamine

HRID 1191103
Notes
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Reaction equation

HRID 1191103 reaction equation
[CH:1]1([CH2:4][NH:5][C:6]2[CH: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)[N: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[CH: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)[N:7]=2)[CH2:3][CH2:2]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58495645HCID 58495645, compound

Product 1

HCID 584956304-[4-(Cyclopropylmethyl-amino)-pyrimidin-2-yl]-benzylamineYield 96.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve 4-[4-(cyclopropylmethyl-amino)-pyrimidin-2-yl]-N-(tert-butoxycarbonyl)-benzylamine (100 mg, 0.28 mmol) in DCM (3 mL) containing trifluoroacetic acid (2 mL). Stir under nitrogen for 3 h. Concentrate in vacuo and purify the crude mixture by SCX chromatography (5 g) to obtain the title compound (68.5 mg, 90%) 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-4b0b3de746a448b5a31b10ea8207b7bd
Source dataset
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08680091B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes