1,3-Dimethyl-2-imidazolidinone → HCID 10291715, compound

HRID 1592928Notes

Reaction equation

HRID 1592928 reaction equation
[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([NH:6][C:7]2[C:8]3[CH:15]=[C:14]([C:16]4[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][CH:17]=4)[O:13][C:9]=3[N:10]=[CH:11][N:12]=2)=[C:4]([F:27])[CH:3]=1.C(N(CC)CC)C.CN1C(=O)N(C)CC1>C1COCC1.[Ni]>[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([NH:6][C:7]2[C:8]3[CH:15]=[C:14]([C:16]4[CH:17]=[CH:18][C:19]([NH2:22])=[CH:20][CH:21]=4)[O:13][C:9]=3[N:10]=[CH:11][N:12]=2)=[C:4]([F:27])[CH:3]=1

Participants

6

Reactant 3

HCID 66611,3-Dimethyl-2-imidazolidinoneHCID 8471TriethylamineHCID 10178104HCID 10178104, compound

Product 1

HCID 10291715HCID 10291715, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

0.95 g (2.5 mmols) of 4-(4-chloro-2-fluoranilino)-6-(4-nitrophenyl)furo[2,3-d]pyrimidine suspended in ca. 50 ml of THF, 2 ml of triethylamine and 2 ml of DMEU, mixed with a spatula tip of catalyst suspension (ethanolic Raney nickel) and shaken over night under H2 at normal pressure. The suspension is filtered by suction through Celite, concentrated by evaporation, mixed with H2O, set at pH 10 with 5% NaOH solution, filtered by suction, and the residue washed with a lot of H2O. The product is worked up by column chromatography (dissolved in acetone and added to the column as a silica gel adsorbate, silica gel, pentane:ethyl acetate=3:2, m.p.: 229-232° C.

Workup

  1. filtrationThe suspension is filtered by suction through Celite
  2. concentrationconcentrated by evaporation
  3. additionmixed with H2O
  4. filtrationfiltered by suction
  5. washthe residue washed with a lot of H2O
  6. dissolutiondissolved in acetone
  7. additionadded to the column as a silica gel adsorbate, silica gel, pentane

Sources & evidence

ORD record
ord-911fbe97b6cc494f94d491058db2a8f1
Source dataset
uspto-grants-2007_11
Patent number
US07294633B2

Reaction notes

Loading…