Methylhydrazine → 2-Methylsulfanyl-pyrimidine-4-carboxylic acid N-methyl-hydrazide

HRID 1838869Notes

Reaction equation

[CH3:1][NH:2][NH2:3].[CH3:4][S:5][C:6]1[N:11]=[C:10]([C:12](Cl)=[O:13])[CH:9]=[CH:8][N:7]=1>C(Cl)Cl>[CH3:1][N:2]([C:12]([C:10]1[CH:9]=[CH:8][N:7]=[C:6]([S:5][CH3:4])[N:11]=1)=[O:13])[NH2:3]

Participants

Conditions

Temperature: -78 °C

Procedure

To a −78° C. stirred solution of methyl hydrazine (17 mL, 318 mmol) in CH2Cl2 (500 mL) is added dropwise a solution of 2-methylsulfanyl-pyrimidine-4-carbonyl chloride (20 g, 106 mmol) in CH2Cl2 (500 mL). The reaction mixture is stirred for 2 hours at −78° C. and then slowly warmed to room temperature. The reaction mixture is concentrated under reduced pressure to give a purple oil. Purification over silica (EtOAc/hexanes 1:1) affords 6.98 g (33% yield) of the desired compound. 1H NMR (300 MHz, CDCl3) δ 8.69-8.64 (m, 1H), 7.35-7.08 (m, 1H), 3.40 (s, 3H), 3.36 (s, 2H), 2.59 (s, 3H); ESI/MS: 199.1 (M+H).

Workup

temperatureslowly warmed to room temperature
concentrationThe reaction mixture is concentrated under reduced pressure
customto give a purple oil
customPurification over silica (EtOAc/hexanes 1:1)

Sources & evidence

ORD record: ord-291b76739ee54a64bf992cd327dfecc0
Source dataset: uspto-grants-2004_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06677337B2

Reaction notes

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