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

HRID 1880184Notes

Reaction equation

HRID 1880184 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-e9f4c2ebf1794ebe84602385a8117850
Source dataset
uspto-grants-2012_11
Patent number
US08318718B2

Reaction notes

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