2-Pyridineethanamine → HCID 22308409, compound

HRID 2117644Notes

Reaction equation

HRID 2117644 reaction equation
ClC1N=C(Cl)C=CN=1.[Cl:9][C:10]1[N:15]=[C:14]([NH:16][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)[CH:13]=[CH:12][N:11]=1.NCCC1C=CC=CN=1.C(N(CC)C(C)C)(C)C>C(O)(C)C>[Cl:9][C:10]1[N:15]=[C:14]([NH:16][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)[CH:13]=[CH:12][N:11]=1

Participants

5

Reactant 3

HCID 759192-PyridineethanamineHCID 81531DiisopropylethylamineHCID 86760735HCID 86760735, compound

Product 1

HCID 22308409HCID 22308409, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

(2-Chloropyrimidin-4-yl)-(2-pyridin-2-yl-ethyl)amine 2,4-Dichloropyrimidine (1.43 g, 9.60 mmol) was added to a solution of 2-(2-aminoethyl)pyridine (1.00 g, 8.19 mmol) in isopropanol (10 mL). N,N-Diisopropyl-ethylamine (1.24 g, 1.67 mL, 9.59 mmol) was added and the mixture stirred at room temperature overnight. The resulting suspension was concentrated to afford an off-white solid. This material was purified via column chromatography on silica gel (gradient elution with 0-10% ethanol-dichloromethane) to afford (2-chloropyrim-idin-4-yl)-(2-pyridin-2-yl-ethyl)amine as an off-white solid. MS (MH+) 235; Calculated 234.69 for C11H11ClN4.

Workup

  1. concentrationThe resulting suspension was concentrated
  2. customto afford an off-white solid
  3. customThis material was purified via column chromatography on silica gel (gradient elution with 0-10% ethanol-dichloromethane)

Sources & evidence

ORD record
ord-7ea9b66b811149b5ac0ee44cfa56ff74
Source dataset
uspto-grants-2008_10
Patent number
US07442698B2

Reaction notes

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