Benzylamine → 2-Methylthio-4-(benzyl)amino-5-nitro-6-(3-dimethylaminocarbonylphenoxy)pyrimidine

HRID 1290664Notes

Reaction equation

[CH3:1][S:2][C:3]1[N:8]=[C:7](Cl)[C:6]([N+:10]([O-:12])=[O:11])=[C:5]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([N:22]([CH3:24])[CH3:23])=[O:21])[CH:15]=2)[N:4]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:31]([NH2:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>C(#N)C>[CH3:1][S:2][C:3]1[N:8]=[C:7]([NH:38][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:6]([N+:10]([O-:12])=[O:11])=[C:5]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([N:22]([CH3:24])[CH3:23])=[O:21])[CH:15]=2)[N:4]=1

Participants

Conditions

Temperature: 75 °C

Procedure

In a similar manner, to 2-methylthio-4-chloro-5-nitro-6-(3-dimethylaminocarbonylphenoxy)pyrimidine (3.19 g, 8.65 mmol), a compound of formula (M), in 90 mL acetonitrile at 0° C. was added cesium carbonate (3.66 g, 11.2 mmol), followed by the addition of benzylamine (0.95 mL, 8.65 mmol). The reaction mixture was heated at 75° C. for 4 hours. The reaction mixture was filtered, the filtrate evaporated and the residue chromatographed on silica gel (ethyl acetate:methanol, 10:1) to afford 1.76 g (48%) of 2-methylthio-4-(benzyl)amino-5-nitro-6-(3-dimethylaminocarbonylphenoxy)pyrimidine, a compound of formula (N).

Workup

filtrationThe reaction mixture was filtered
customthe filtrate evaporated
customthe residue chromatographed on silica gel (ethyl acetate:methanol, 10:1)

Sources & evidence

ORD record: ord-13c5ab4aa0a84c60a0758c2d233108c4
Source dataset: uspto-grants-1998_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05753635

Reaction notes

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