Potassium Phosphate, Tribasic → 4-chloro-5-(3,6-dihydro-2H-pyran-4-yl)pyrimidine

HRID 410319Notes

Reaction equation

HRID 410319 reaction equation
P([O-])([O-])([O-])=O.[K+].[K+].[K+].[Cl:9][C:10]1[C:15](I)=[CH:14][N:13]=[CH:12][N:11]=1.[O:17]1[CH2:22][CH:21]=[C:20](B2OC(C)(C)C(C)(C)O2)[CH2:19][CH2:18]1>COCCOC.O.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.[Fe+2].C(O[Pd]OC(=O)C)(=O)C>[Cl:9][C:10]1[C:15]([C:20]2[CH2:21][CH2:22][O:17][CH2:18][CH:19]=2)=[CH:14][N:13]=[CH:12][N:11]=1

Participants

8

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 112180533,6-Dihydro-2H-pyran-4-boronic acid pinacol esterHCID 112302044-Chloro-5-iodopyrimidine

Product 1

HCID 593268324-chloro-5-(3,6-dihydro-2H-pyran-4-yl)pyrimidine

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 962WaterSolvent2×HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

To a 150 mL sealable flask was added potassium phosphate (4.21 g, 19.83 mmol), dppf (0.264 g, 0.476 mmol), diacetoxypalladium (0.053 g, 0.238 mmol), 4-chloro-5-iodopyrimidine (1.907 g, 7.93 mmol), and 2-(3,6-dihydro-2H-pyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1.75 g, 8.33 mmol) as a solution in DME (45.3 mL)/water (7.56 mL). The vessel was sealed and heated to 80° C. for 20 h. The reaction mixture was cooled to room temperature and diluted with water before extracting with ethyl acetate. The combined organics were dried over sodium sulfate, filtered, and concentrated under reduced pressure to a dark brown oil that was used without purification. MS (ESI, pos. ion) m/z: 176.2 (M+1).

Workup

  1. customThe vessel was sealed
  2. temperatureThe reaction mixture was cooled to room temperature
  3. extractionbefore extracting with ethyl acetate
  4. dry with materialThe combined organics were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure to a dark brown oil that
  7. customwas used without purification

Sources & evidence

ORD record
ord-ddac7db3e3b54dd7b8bbbe0e84b6c957
Source dataset
uspto-grants-2014_06
Patent number
US08759532B2

Reaction notes

Loading…