Methanol → HCID 22398430, compound

HRID 1363893Notes

Reaction equation

HRID 1363893 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[NH:10][C:11]1[CH:16]=[CH:15][N:14]=[C:13]([NH:17][C:18]2[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[CH:20][CH:19]=2)[N:12]=1.C[OH:27]>O>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[NH:10][C:11]1[CH:16]=[CH:15][N:14]=[C:13]([NH:17][C:18]2[CH:25]=[CH:24][C:21]([C:22]([NH2:23])=[O:27])=[CH:20][CH:19]=2)[N:12]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 214347Dapivirine

Product 1

HCID 22398430HCID 22398430, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-[[4-[(2,4,6-trimethylphenyl)amino]-2-pyrimidinyl]amino]benzonitrile (0.00303 mol) and NaBO3.4H2O (0.00911 mol) in CH3OH (30 ml) and H2O (10 ml) was stirred and refluxed for 4 days. The reaction mixture was cooled. The precipitate was filtered off and the precipitate (!) was purified by flash column chromatography over silica gel (eluent: CH2Cl2/CH3OH gradient from 100/0 to 95/5). The desired fractions were collected and the solvent was evaporated, yielding 0.586 g (56%) of 4-[[4-[(2,4,6-trimethylphenyl)amino]-2-pyrimidinyl]amino]benzamide (comp. 40). The filtrate (!) was purified by reversed-phase HPLC (eluent gradient: ((0.5% ammoniumacetate in H2O)/CH3CN 90/10)/CH3OH/CH3CN (0 minutes) 75/25/0, (44 minutes) 0/50/50, (57 minutes) 0/0/100, (61.1-70 minutes) 75/25/0). Three desired fraction groups were collected and their solvent was evaporated, yielding 0.18 g of 4-[[4-[(2,4,6-trimethylphenyl)amino]-2-pyrimidinyl]amino]benzamide, N3-oxide (comp. 49) and 0.030 g of 4-[[4-(2,4,6-trimethylphenyl)amino]-2-pyrimidinyl]-amino]benzamide, N1-oxide.

Workup

  1. temperaturerefluxed for 4 days
  2. temperatureThe reaction mixture was cooled
  3. filtrationThe precipitate was filtered off
  4. customthe precipitate (!) was purified by flash column chromatography over silica gel (eluent: CH2Cl2/CH3OH gradient from 100/0 to 95/5)
  5. customThe desired fractions were collected
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-c41d92c8337f4e4394c552fd77cc5138
Source dataset
uspto-grants-2011_02
Patent number
US07887845B2

Reaction notes

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