Hydrochloric Acid → HCID 18763650, compound

HRID 431258Notes

Reaction equation

HRID 431258 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([N:8]2[CH2:12][CH2:11][CH2:10][CH2:9]2)[N:5]=[C:4](/[CH:13]=[CH:14]/[C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-])=O)[CH:16]=2)[N:3]=1.Cl.[OH-].[Na+]>C(O)C>[CH3:1][C:2]1[CH:7]=[C:6]([N:8]2[CH2:12][CH2:11][CH2:10][CH2:9]2)[N:5]=[C:4](/[CH:13]=[CH:14]/[C:15]2[CH:16]=[C:17]([NH2:21])[CH:18]=[CH:19][CH:20]=2)[N:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 18763633HCID 18763633, compound

Product 1

HCID 18763650HCID 18763650, compoundYield 65.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 480 mg (1.57 mmol) of (E)-4-methyl-2-[2-(3-nitro-phenyl)-vinyl]-6-pyrrolidin-1-yl-pyrimidine in 12 ml ethanol were added at RT 1.41 g (6.28 mmol) stannous chloride dihydrate followed by dropwise addition of 1 ml 36% HCl. The mixture was stirred at RT for 12 h, the pH adjusted to pH 7 by dropwise addition of 3N NaOH and then extracted several times with AcOEt. The organic layers were combined, dried over Na2SO4 and concentrated in vacuo. The residue was applied to a silica gel column with CH2Cl2/MeOH (10/1) as eluent. Combination of the purified fractions and evacuation in vacuo gave 289 mg (65.7%) of the desired (E)-3-[2-(4-methyl-6-pyrrolidin-1-yl-pyrimidin-2-yl)-vinyl]-phenylamine as a yellow solid. ISP mass spectrum, m/e: 281.2 (M+1 calculated for C17H20N4: 281).

Workup

  1. extractionextracted several times with AcOEt
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-73efae66924440f2bcca824e4a4985ee
Source dataset
uspto-grants-2003_12
Patent number
US06657060B2

Reaction notes

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