5-Bromo-2-iodopyrimidine → HCID 86696907, compound

HRID 1399996Notes

Reaction equation

HRID 1399996 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5](I)=[N:6][CH:7]=1.[O:9]1[CH2:14][CH:13]=[C:12](B2OC(C)(C)C(C)(C)O2)[CH2:11][CH2:10]1>O1CCOCC1.O>[Br:1][C:2]1[CH:3]=[N:4][C:5]([C:12]2[CH2:13][CH2:14][O:9][CH2:10][CH:11]=2)=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 70066515-Bromo-2-iodopyrimidineHCID 112180533,6-Dihydro-2H-pyran-4-boronic acid pinacol ester

Product 1

HCID 86696907HCID 86696907, compound

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
80 °C

Procedure

5-bromo-2-iodo-pyrimidine (250 mg; 0.88 mmol) and 2-(3,6-dihydro-2H-pyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (196 mg, 0.92 mmol) were dissolved in 1,4-dioxane-H2O (10:1; 10 mL) and degassed with a stream of N2 for 10 min. Pd(Ph3)2Cl2 (30 mg, 0.04 mmol) was introduced and the reaction sealed and heated in a microwave reactor for 30 min at 80° C. The reaction was concentrated in vacuo, re-dissolved in DCM, filtered and purified over silica (gradient elution, 0-50% EtOAc-n-heptane) yielding i (105 mg, 50%). MS: 241.1 & 243.0; 1:1 [M+H]+.

Workup

  1. customdegassed with a stream of N2 for 10 min
  2. customthe reaction sealed
  3. concentrationThe reaction was concentrated in vacuo
  4. dissolutionre-dissolved in DCM
  5. filtrationfiltered
  6. custompurified over silica (gradient elution, 0-50% EtOAc-n-heptane)
  7. customyielding i (105 mg, 50%)

Sources & evidence

ORD record
ord-d00ddccfe3d54a7a9f9e4a71596ebeaa
Source dataset
uspto-grants-2014_12
Patent number
US08906902B2

Reaction notes

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