Hydrochloric Acid → HCID 59363802, compound

HRID 2189179Notes

Reaction equation

HRID 2189179 reaction equation
Cl[C:2]1[N:7]=[C:6](Cl)[CH:5]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:15][CH2:16][CH2:17][CH:18]([CH3:20])[CH3:19])[N:3]=1.CC1(C)C(C)(C)OB([C:29]2[CH:38]=[CH:37][C:32]3[NH:33][C:34](=[O:36])[NH:35][C:31]=3[CH:30]=2)O1.C([O-])(O)=[O:41].[Na+].Cl>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C1COCC1>[CH3:19][CH:18]([CH3:20])[CH2:17][CH2:16][O:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[C:4]1[NH:3][C:2](=[O:41])[N:7]=[C:6]([C:29]2[CH:38]=[CH:37][C:32]3[NH:33][C:34](=[O:36])[NH:35][C:31]=3[CH:30]=2)[CH:5]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 438110655-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzo[d]imidazol-2(3H)-oneHCID 57445459HCID 57445459, compound

Product 1

HCID 59363802HCID 59363802, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

A round bottom flask was charged with 2,4-dichloro-6-(2-(isopentyloxy)phenyl)pyrimidine (100 mg, 0.32 mmol), 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzo[d]imidazol-2(3H)-one (91 mg, 0.35 mmol), Pd(dppf)Cl2 (3 mol %), 1 M NaHCO3 (0.3 mL), and THF (5 mL). The reaction mixture was heated to 70° C. for 2 hours. The reaction mixture was allowed to cool down to the room temperature, and 4 mL of conc. HCl was slowly added. The resulting slurry was heated to 100° C. for an additional 5 hours. The mixture was cooled down to room temperature, filtered, and concentrated under reduced pressure. The product was purified by preparative HPLC to result in 5-(6-{2-[(3-methylbutyl)oxy]phenyl}-2-oxo-1,2-dihydropyrimidin-4-yl)-1,3-dihydro-2H-benzimidazol-2-one. 1H NMR (400 MHz, d6-DMSO): δ 10.95 (s, 2H), 7.81-7.75 (m, 3H), 7.53 (t, 1H), 7.20 (d, 1H), 7.14-7.05 (m, 2H), 4.08 (t, 2H), 1.80-1.60 (m, 3H), 0.85 (s, 6H). MS (EI) for C22H22N4O3: 391 (MH+).

Workup

  1. additionwas slowly added
  2. temperatureThe resulting slurry was heated to 100° C. for an additional 5 hours
  3. temperatureThe mixture was cooled down to room temperature
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe product was purified by preparative HPLC
  7. customto result in 5-(6-{2-[(3-methylbutyl)oxy]phenyl}-2-oxo-1,2-dihydropyrimidin-4-yl)-1,3-dihydro-2H-benzimidazol-2-one

Sources & evidence

ORD record
ord-548fde196f854f968551b978c55a47cf
Source dataset
uspto-grants-2012_12
Patent number
US08324231B2

Reaction notes

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