Triethylamine → Tert-butyl 3-(6-(dibenzylamino)-5-nitropyrimidin-4-ylamino)phenyl(methyl)carbamate

HRID 1887050Notes

Reaction equation

HRID 1887050 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([N:8]([CH3:16])[C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH:5]=[CH:6][CH:7]=1.[CH2:17]([N:24]([CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:25]1[C:30]([N+:31]([O-:33])=[O:32])=[C:29](Cl)[N:28]=[CH:27][N:26]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.CCN(CC)CC>O1CCOCC1>[CH2:35]([N:24]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:25]1[N:26]=[CH:27][N:28]=[C:29]([NH:1][C:2]2[CH:3]=[C:4]([N:8]([CH3:16])[C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:13])[CH3:14])[CH:5]=[CH:6][CH:7]=2)[C:30]=1[N+:31]([O-:33])=[O:32])[C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11492276tert-butyl N-(3-aminophenyl)-N-methylcarbamateHCID 23477266N,N-dibenzyl-6-chloro-5-nitropyrimidin-4-amine

Product 1

HCID 86761989Tert-butyl 3-(6-(dibenzylamino)-5-nitropyrimidin-4-ylamino)phenyl(methyl)carbamateYield 63%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of tert-butyl 3-aminophenyl(methyl)carbamate (20) (4.6 g, 20.8 mmol) and N,N-dibenzyl-6-chloro-5-nitropyrimidin-4-amine (1) (7 g, 19.8 mmol) in dioxane (100 mL) was added Et3N (6 mL) and the reaction mixture was stirred at 60° C. overnight. The mixture was cooled to room temperature, the solvent was evaporated before water (200 mL) and EA (100 mL) was introduced. Organic layer was separated and extracted with EA (60 mL×2). After the organic layer was washed with brine and dried over anhydrous sodium sulfate, the solvent was evaporated. The residue was purified by column chromatography (silica gel, 0 to 30% ethyl acetate in petroleum ether) to give tert-butyl 3-(6-(dibenzylamino)-5-nitropyrimidin-4-ylamino)phenyl(methyl)carbamate (21) 6.7 g as yellow solid (yield 63%). LC-MS (ESI): m/z (M+1) 541.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customthe solvent was evaporated before water (200 mL) and EA (100 mL)
  3. additionwas introduced
  4. customOrganic layer was separated
  5. extractionextracted with EA (60 mL×2)
  6. washAfter the organic layer was washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customthe solvent was evaporated
  9. customThe residue was purified by column chromatography (silica gel, 0 to 30% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-ee719c48150f402aa4399fa6f23bdcb4
Source dataset
uspto-grants-2013_08
Patent number
US08501724B1

Reaction notes

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