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Trifluoroacetic acid → 4-(4-(Mesityloxy)-5-methyl-5H-pyrrolo[3,2-d]pyrimidin-2-ylamino)benzonitrile

HRID 1516853
Notes
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Reaction equation

HRID 1516853 reaction equation
Cl[C:2]1[N:3]=[C:4]([O:12][C:13]2[C:18]([CH3:19])=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=2[CH3:21])[C:5]2[N:10]([CH3:11])[CH:9]=[CH:8][C:6]=2[N:7]=1.[NH2:22][C:23]1[CH:30]=[CH:29][C:26]([C:27]#[N:28])=[CH:25][CH:24]=1.C(O)(C(F)(F)F)=O>O>[C:14]1([CH3:21])[CH:15]=[C:16]([CH3:20])[CH:17]=[C:18]([CH3:19])[C:13]=1[O:12][C:4]1[C:5]2[N:10]([CH3:11])[CH:9]=[CH:8][C:6]=2[N:7]=[C:2]([NH:22][C:23]2[CH:30]=[CH:29][C:26]([C:27]#[N:28])=[CH:25][CH:24]=2)[N:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 133964-AminobenzonitrileHCID 576936612-Chloro-4-(mesityloxy)-5-methyl-5H-pyrrolo[3,2-d]pyrimidine

Product 1

HCID 576936284-(4-(Mesityloxy)-5-methyl-5H-pyrrolo[3,2-d]pyrimidin-2-ylamino)benzonitrileYield 95.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

In a sealed tube was added 2-chloro-4-(mesityloxy)-5-methyl-5H-pyrrolo[3,2-d]pyrimidine (52.7 mg, 0.18 mmol), 4-aminobenzonitrile (83 mg, 0.70 mmol), TFE (1.0 mL) and TFA (0.11 mL, 1.44 mmol). The reaction mixture was stirred at 90° C. for 48 h. Upon completion of the reaction, the resulting mixture was cooled, diluted with water and washed with EtOAc. The combined organic layers were washed with NaHCO3, brine, dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by preparative TLC, eluting with hexanes:ethyl acetate (5:1-2:1), to give the product as a light yellow solid (65.7 mg, 95%).

Workup

  1. customUpon completion of the reaction
  2. temperaturethe resulting mixture was cooled
  3. washwashed with EtOAc
  4. washThe combined organic layers were washed with NaHCO3, brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by preparative TLC
  9. washeluting with hexanes:ethyl acetate (5:1-2:1)

Sources & evidence

ORD record
ord-57c8682133874f08a8e3addf321fb291
Source dataset
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08227601B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes