4-Pyridinemethanamine → HCID 44413030, compound

HRID 749110Notes

Reaction equation

HRID 749110 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1.[N+](C1C=CC([O:18][C:19](=O)[N:20]([C:31]2[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=2)[C:21]2[CH:26]=[CH:25][N:24]=[C:23]([NH:27][CH:28]([CH3:30])[CH3:29])[N:22]=2)=CC=1)([O-])=O>C(Cl)Cl>[F:37][C:34]1[CH:33]=[CH:32][C:31]([N:20]([C:21]2[CH:26]=[CH:25][N:24]=[C:23]([NH:27][CH:28]([CH3:30])[CH3:29])[N:22]=2)[C:19]([NH:1][CH2:2][C:3]2[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=2)=[O:18])=[CH:36][CH:35]=1

Participants

4

Reactant 2

HCID 773174-PyridinemethanamineHCID 59751988HCID 59751988, compound

Product 1

HCID 44413030HCID 44413030, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-(Aminomethyl)pyridine (100 μL, 0.974 mmol) is added dropwise to a solution of (4-fluorophenyl)-(2-isopropylamino-pyrimidin-4-yl)-carbamic acid 4-nitro-phenyl ester, 5, (334 mg, 0.812 mmol) in methylene chloride (8 mL) at room temperature. The orange solution is stirred at ambient temperature overnight. The reaction mixture is diluted with methylene chloride (50 mL) and washed with a 0.5 N aqueous solution of sodium hydroxide (2×50 mL) and water (50 mL), dried over sodium sulfate, filtered and concentrated to a yellow oil which is purified over silica (20% Et2O/CH2Cl2 to 100% EtOAc) to afford the desired product as a white solid: 1H NMR (300 MHz, CDCl3) δ 10.76 (br s, 1H), 8.61 (d, J=6.0 Hz, 2H), 7.93 (d, J=5.7 Hz, 1H), 7.34 (d, J=6.0 Hz, 2H), 7.29-7.16 (m, 4H), 5.43 (d, J=5.9 Hz, 1H), 5.02 (br s, 1H), 4.60 (d, J=5.5 Hz, 2H), 4.15 (br s, 1H), 1.15 (d, J=6.4 Hz, 6H); MS (ESI) m/z 381 (M+1).

Workup

  1. washwashed with a 0.5 N aqueous solution of sodium hydroxide (2×50 mL) and water (50 mL)
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated to a yellow oil which
  5. customis purified over silica (20% Et2O/CH2Cl2 to 100% EtOAc)

Sources & evidence

ORD record
ord-83c6a1f97eeb4a759d1acb19b0cf89ec
Source dataset
uspto-grants-2008_07
Patent number
US07402589B2

Reaction notes

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