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

HRID 2222239Notes

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-ff904a66f36c4064b01ae18d75e4b3e2
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07371750B2

Reaction notes

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