Diisopropylethylamine → 2-(1H-pyrrol-1-yl)pyrimidine

HRID 896240Notes

Reaction equation

HRID 896240 reaction equation
C[CH2:2][N:3]([CH:7]([CH3:9])C)[CH:4]([CH3:6])C.Cl[C:11]1[N:16]=[C:15]([N:17]2[CH:21]=[CH:20][CH:19]=[CH:18]2)[CH:14]=[C:13](Cl)[N:12]=1>C(O)(C(F)(F)F)=O.C(Cl)Cl.O>[N:3]1([C:2]2[N:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[CH:4]=[CH:6][CH:9]=[CH:7]1.[N:17]1([C:15]2[CH:14]=[CH:13][N:12]=[CH:11][N:16]=2)[CH:18]=[CH:19][CH:20]=[CH:21]1

Participants

6

Reactant 2

HCID 81531DiisopropylethylamineHCID 223499872,4-Dichloro-6-(1H-pyrrol-1-yl)pyrimidine

Product 2

HCID 47151112-(1H-pyrrol-1-yl)pyrimidineHCID 22349989HCID 22349989, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Conditions

Temperature
80 °C

Procedure

A solution of the amide 143 (200 mg, 0.5 mmol) in 10 mL of TFA:DCM (1:1) was stirred at RT for two days. The solvent was evaporated and the residue was taken in 5 mL of DMF containing DIEA (258 mg, 2.0 mmol) and 2,6-dichloro-4-(1-pyrrolyl)pyrimidine (107 mg, 0.5 mmol). After heating overnight at 80° C., the reaction mixture was diluted with water and the product was extracted into ethyl acetate. The solvent was removed and the residue was chromatographed (silica gel, hexane:ethyl acetate (1:3)) to give 50 mg of the 2-(1-pyrrolyl)pyrimidine derivative and 58 mg of the 4-(1-pyrrolyl)pyrimidine compound 144, (M+H)+: 477.3

Workup

  1. customThe solvent was evaporated
  2. extractionthe product was extracted into ethyl acetate
  3. customThe solvent was removed
  4. customthe residue was chromatographed (silica gel, hexane:ethyl acetate (1:3))

Sources & evidence

ORD record
ord-b0a267262fec45aba0518670f544c0fb
Source dataset
uspto-grants-2005_07
Patent number
US06919347B2

Reaction notes

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