Sodium Carbonate → HCID 70022417, compound

HRID 398038Notes

Reaction equation

HRID 398038 reaction equation
[NH2:1][C@@H:2]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:3][NH:4][C:5]1[N:10]=[C:9]([C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)[C:8](Br)=[CH:7][N:6]=1.C(=O)([O-])[O-].[Na+].[Na+].[Cl:31][C:32]1[CH:33]=[C:34](B(O)O)[CH:35]=[CH:36][C:37]=1[F:38]>C1(C)C=CC=CC=1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[ClH:31].[NH2:1][C@@H:2]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:3][NH:4][C:5]1[N:10]=[C:9]([C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)[C:8]([C:34]2[CH:35]=[CH:36][C:37]([F:38])=[C:32]([Cl:31])[CH:33]=2)=[CH:7][N:6]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27346603-Chloro-4-fluorophenylboronic Acid (contains varying amounts of Anhydride)HCID 22084576HCID 22084576, compound

Product 1

HCID 70022417HCID 70022417, compound

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 1140TolueneSolvent2×

Procedure

A mixture of 2-((2(S)-amino-3-phenyl propyl)amino)-5-bromo-4-(4-pyridyl)-pyrimidine (204 mg, 0.53 mmol), aqueous 2M sodium carbonate (1.66 ml, 3.32 mmol) and 3-chloro-4-fluorobenzene boronic acid (103 mg, 0.637 mmol) in toluene (5 ml) was stirred for 10 min under argon. The mixture was thoroughly degassed (10 times), before the addition of tetrakis (triphenylphosphine) palladium(0) (18 mg, 0.016 mmol). After heating at reflux for 16 h, the reaction mixture was diluted with toluene and washed with brine. The organic solution was dried and evaporated. Subsequent column chromatography on silica gel (dichloromethane-methanol-conc. ammonium hydroxide=95:5:04) provided the title compound which was converted into the hydrochloride by the addition of 6N hydrochloric acid (64 •l) to its methanolic solution (2 ml) followed by evaporation. MS (m/z): 434.1 (M)+; C24H21ClFN5 requir. 433.9 (free base).

Workup

  1. customThe mixture was thoroughly degassed (10 times)
  2. temperatureAfter heating
  3. temperatureat reflux for 16 h
  4. washwashed with brine
  5. customThe organic solution was dried
  6. customevaporated

Sources & evidence

ORD record
ord-e44d86c7bf1c4ab0ae5d0868da2f3f12
Source dataset
uspto-grants-2003_08
Patent number
US06610698B2

Reaction notes

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