Trifluoroacetic acid → 2-(2-(2-(2-((4-(Aminomethyl)phenyl)amino)-5-methylpyrimidin-4-yl)ethyl)phenyl)acetamide

HRID 1779081Notes

Reaction equation

HRID 1779081 reaction equation
C(O)(C(F)(F)F)=O.[NH2:8][C:9](=[O:42])[CH2:10][C:11]1[CH:41]=[CH:40][CH:39]=[CH:38][C:12]=1[CH2:13][CH2:14][C:15]1[C:20]([CH3:21])=[CH:19][N:18]=[C:17]([NH:22][C:23]2[CH:37]=[CH:36][C:26]([CH2:27][NH:28]C(=O)OC(C)(C)C)=[CH:25][CH:24]=2)[N:16]=1>C(Cl)Cl>[NH2:28][CH2:27][C:26]1[CH:25]=[CH:24][C:23]([NH:22][C:17]2[N:16]=[C:15]([CH2:14][CH2:13][C:12]3[CH:38]=[CH:39][CH:40]=[CH:41][C:11]=3[CH2:10][C:9]([NH2:8])=[O:42])[C:20]([CH3:21])=[CH:19][N:18]=2)=[CH:37][CH:36]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86712717tert-Butyl 4-((4-(2-(2-amino-2-oxoethyl)phenethyl)-5-methylpyrimidin-2-yl)amino)benzylcarbamate

Product 1

HCID 730557472-(2-(2-(2-((4-(Aminomethyl)phenyl)amino)-5-methylpyrimidin-4-yl)ethyl)phenyl)acetamideYield 82.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (1 mL) was added to a solution of tert-butyl 4-((4-(2-(2-amino-2-oxoethyl)phenethyl)-5-methylpyrimidin-2-yl)amino)benzylcarbamate (A114) (0.043 g, 0.090 mmol) in DCM (3 mL) and the resulting solution stirred at room temperature for 4 hours. The volatiles were removed in vacuo then 2 M aqueous K2CO3 (5 mL) and water (15 mL) were added to the residue. The resulting suspension was sonicated for 1 minute, filtered and the filter cake dried to give the title compound 27 as a light tan solid (0.028 g, 82%); 1H NMR (300 MHz, d6-DMSO) δ 9.30 (s, 1H), 8.16 (s, 1H), 7.70 (d, J=8.5 Hz, 2H), 7.43 (s, 1H), 7.12-7.27 (m, 6H), 6.93 (s, 1H), 3.64 (s, 2H), 3.49 (s, 2H), 3.34 (brs, 2H), 3.02-3.07 (m, 2H), 2.85-2.90 (m, 2H), 2.06 (s, 3H). LCMS-B: rt 4.666 min; m/z 376 [M+H]+.

Workup

  1. customThe volatiles were removed in vacuo
  2. addition2 M aqueous K2CO3 (5 mL) and water (15 mL) were added to the residue
  3. customThe resulting suspension was sonicated for 1 minute
  4. filtrationfiltered
  5. customthe filter cake dried

Sources & evidence

ORD record
ord-e333dd37f9ec426ba3bad39ad5d70eda
Source dataset
uspto-grants-2016_02
Patent number
US09266864B2

Reaction notes

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