2-Methyl-4-nitroaniline → HCID 24747271, compound

HRID 1988584Notes

Reaction equation

[NH2:1][C:2]1[C:7]([CH:8]=O)=[CH:6][N:5]=[C:4]([S:10][CH3:11])[N:3]=1.C[C:13]1[CH:18]=[C:17]([N+:19]([O-:21])=[O:20])[CH:16]=[CH:15][C:14]=1N.[C:23]([BH3-])#[N:24].[Na+]>CN(C=O)C.CC(O)=O.CCO.CCOC(C)=O>[CH3:13][C:14]1[CH:15]=[CH:16][C:17]([N+:19]([O-:21])=[O:20])=[CH:18][C:23]=1[NH:24][CH2:8][C:7]1[C:2]([NH2:1])=[N:3][C:4]([S:10][CH3:11])=[N:5][CH:6]=1

Participants

Conditions

Temperature: 40 °C

Procedure

4-amino-2-methylsulfanyl-pyrimidine-5-carbaldehyde (1.80 g, 10.6 mmol) and 2-methyl-4-nitrophenylamine (1.94 g, 12.8 mmol) is dissolved in the mixed solvent of DMF (18 mL), AcOH (18 mL), and EtOH (36 mL), and the reaction mixture is stirred for 2 hours at 40° C. To the reaction mixture is added sodium cyanoborohydride (2.01 g, 31.2 mmol) and the mixture is stirred for 30 minutes at room temperature. The reaction mixture is diluted with EtOAc (80 mL), and washed with saturated aqueous sodium bicarbonate solution. The organic layer is dried over MgSO4, and concentrated under reduced pressure. The residue is purified by flash column chromatography (SiO2, EtOAc/hexane=1/2) to give 5-[(2-methyl-5-nitro-phenylamino)-methyl]-2-methylsulfanyl-pyrimidin-4-ylamine (1.10 g, 34%) as an orange solid.

Workup

stirringthe mixture is stirred for 30 minutes at room temperature
washwashed with saturated aqueous sodium bicarbonate solution
dry with materialThe organic layer is dried over MgSO4
concentrationconcentrated under reduced pressure
customThe residue is purified by flash column chromatography (SiO2, EtOAc/hexane=1/2)

Sources & evidence

ORD record: ord-5d5dee3ae68c43c4a53015708df0b4dd
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07642255B2

Reaction notes

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