Tetrahydrofuran → N'-(5-cyano-2-methylsulfanyl-pyrimidin-4-yl)-hydrazinecarboxylic acid tert-butyl ester

HRID 1818730Notes

Reaction equation

HRID 1818730 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[C:4]([S:10][CH3:11])[N:3]=1.[C:12]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])(=[O:15])[NH:13][NH2:14].C(N(CC)CC)C.C1COCC1>C(OCC)C>[C:17]([O:16][C:12]([NH:13][NH:14][C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[C:4]([S:10][CH3:11])[N:3]=1)=[O:15])([CH3:20])([CH3:19])[CH3:18]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 70091tert-Butyl carbazateHCID 131141834-Chloro-2-(methylsulfanyl)pyrimidine-5-carbonitrile

Product 1

HCID 68821575N'-(5-cyano-2-methylsulfanyl-pyrimidin-4-yl)-hydrazinecarboxylic acid tert-butyl esterYield 83%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

4-Chloro-2-methylsulfanyl-pyrimidine-5-carbonitrile (prepared as described in US2003158218, 0.509 g, 2.74 mmol), tert-butyl carbazate (tert-butoxycarbonyl hydrazine, 0.403 g, 3.05 mmol) and triethylamine (0.57 mL, 4.1 mmol) were added to 25 mL THF. The reaction mixture was stirred 22 hours, and then 25 mL diethyl ether was added and the reaction mixture was filtered through Celite. The filtrate was concentrated under reduced pressure and the resulting oil was chromatographed through silica (0%-33% EtOAc in hexanes) to give 0.64 g of N′-(5-cyano-2-methylsulfanyl-pyrimidin-4-yl)-hydrazinecarboxylic acid tert-butyl ester.

Workup

  1. filtrationthe reaction mixture was filtered through Celite
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customthe resulting oil was chromatographed through silica (0%-33% EtOAc in hexanes)

Sources & evidence

ORD record
ord-a52dac3bcc694705a57a1149f455b3bb
Source dataset
uspto-grants-2009_10
Patent number
US07601726B2

Reaction notes

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