Dimethylformamide → 2-chloro-4-phenyl-6,7-dihydro-5H-cyclopenta[d]pyrimidine

HRID 406853Notes

Reaction equation

HRID 406853 reaction equation
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[CH2:10][CH2:9][CH2:8][C:6]=2[N:7]=1.[C:12]1(B(O)O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C.CN(C)C=O>C(OCC)(=O)C.O>[Cl:1][C:2]1[N:3]=[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:5]2[CH2:10][CH2:9][CH2:8][C:6]=2[N:7]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 66827Phenylboronic AcidHCID 2313312,4-dichloro-5H,6H,7H-cyclopenta(d)pyrimidine

Product 1

HCID 576629772-chloro-4-phenyl-6,7-dihydro-5H-cyclopenta[d]pyrimidineYield 52%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a round bottomed flask containing 2,4-dichloro-6,7-dihydro-5H-cyclopenta[d]pyrimidine (1.85 g, 10.5 mmol) was added phenylboronic acid (1.43 g, 11.8 mmol), dichloro-((bis-diphenylphosphino)ferrocenyl)-palladium (II) (complex with methylene chloride), (800 mg, 0.98 mmol), triethylamine (4.1 mL, 29 mmol), dimethylformamide (30 mL), and water (2 mL). The reaction mixture was heated to 80° C. for 14 h, then cooled to rt and diluted with ethyl acetate. The organic layer was washed with saturated sodium bicarbonate, dried over sodium sulfate, filtered, and concentrated on a rotary evaporator. The material was purified by flash column chromatography to afford 2-chloro-4-phenyl-6,7-dihydro-5H-cyclopenta[d]pyrimidine (1.25 g, 52%) as an off-white solid.

Workup

  1. temperaturecooled to rt
  2. washThe organic layer was washed with saturated sodium bicarbonate
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated on a rotary evaporator
  6. customThe material was purified by flash column chromatography

Sources & evidence

ORD record
ord-f720f3e0738844a592754d44c0829caf
Source dataset
uspto-grants-2014_06
Patent number
US08754092B2

Reaction notes

Loading…