tert-butyl N-((3-(aminomethyl)phenyl)methyl)carbamate → {3-[(5-Nitro-4-thiocyanato-pyrimidin-2-ylamino)-methyl]-benzyl}-carbamic acid tert-butyl ester

HRID 1819475Notes

Reaction equation

HRID 1819475 reaction equation
Cl[C:2]1[N:7]=[C:6]([S:8][C:9]#[N:10])[C:5]([N+:11]([O-:13])=[O:12])=[CH:4][N:3]=1.[C:14]([O:18][C:19](=[O:30])[NH:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28][NH2:29])[CH:23]=1)([CH3:17])([CH3:16])[CH3:15]>CCO>[C:14]([O:18][C:19](=[O:30])[NH:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28][NH:29][C:2]2[N:7]=[C:6]([S:8][C:9]#[N:10])[C:5]([N+:11]([O-:13])=[O:12])=[CH:4][N:3]=2)[CH:23]=1)([CH3:17])([CH3:15])[CH3:16]

Participants

4

Reactant 2

HCID 2756043tert-butyl N-((3-(aminomethyl)phenyl)methyl)carbamateHCID 210775882-Chloro-5-nitropyrimidin-4-yl thiocyanate

Product 1

HCID 57885599{3-[(5-Nitro-4-thiocyanato-pyrimidin-2-ylamino)-methyl]-benzyl}-carbamic acid tert-butyl esterYield 56.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-chloro-5-nitro-4-thiocyanato-pyrimidine (1.31 g, 6.05 mmol) in EtOH (10 mL) at 0° C. was added a solution of (3-aminomethyl-benzyl)-carbamic acid tert-butyl ester (1.43 g, 6.05 mmol) dropwise over 45 min. The reaction was allowed to stir at room temperature overnight and the resulting precipitate filtered and washed with EtOH. The crude material was purified by column chromatography (silica gel, 10:90 to 12:88 EtOAc/hexane) to afford {3-[(5-nitro-4-thiocyanato-pyrimidin-2-ylamino)-methyl]-benzyl}-carbamic acid tert-butyl ester (1.43 g, 56%) as a yellow solid.

Workup

  1. filtrationthe resulting precipitate filtered
  2. washwashed with EtOH
  3. customThe crude material was purified by column chromatography (silica gel, 10:90 to 12:88 EtOAc/hexane)

Sources & evidence

ORD record
ord-e9f09ac04c6149379f9f06c532788f9d
Source dataset
uspto-grants-2009_10
Patent number
US07601714B2

Reaction notes

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