1,2-Dimethoxyethane → HCID 66955906, compound

HRID 1399591Notes

Reaction equation

HRID 1399591 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([OH:14])[CH:9]=2)[C:5]([CH2:15][C:16]([O:18][CH3:19])=[O:17])=[C:4]([CH3:20])[N:3]=1.[C:21]1(B(O)O)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[CH:30](N(CC)C(C)C)([CH3:32])[CH3:31].[CH3:39][O:40][CH2:41]COC>O.[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>[CH3:39][O:40][CH2:41][O:14][C:10]1[CH:9]=[C:8]([C:6]2[C:5]([CH:15]([CH2:31][CH2:30][CH3:32])[C:16]([O:18][CH3:19])=[O:17])=[C:4]([CH3:20])[N:3]=[C:2]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[N:7]=2)[CH:13]=[CH:12][CH:11]=1

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 66827Phenylboronic AcidHCID 81531DiisopropylethylamineHCID 86665650HCID 86665650, compound

Product 1

HCID 66955906HCID 66955906, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolvent

Procedure

Methyl 2-(2-chloro-4-(3-hydroxyphenyl)-6-methylpyrimidin-5-yl)acetate (189 mg; 0.646 mmol), benzeneboronic acid (236 mg; 1.937 mmol) and tetrakis(triphenylphosphine) palladium(0) (74.6 mg; 0.065 mmol) were placed in a 5 mL reaction tube and dissolved in a mixture of degassed DME (2.40 mL) and water (0.80 mL). N,N-Diisopropylethylamine (0.397 mL, 2.58 mmol) was added, the tube was sealed and irradiated in a microwave oven at 130° C. for 30 min. The reaction mixture was partitioned between brine and ethyl acetate, the phases were separated and the water layer was extracted with ethyl acetate. The combined organic layers were dried over magnesium sulphate and concentrated under reduced pressure. The crude material was purified by flash chromatography on silica gel using a linear gradient of ethylacetate (10-80%) in heptane to give 172 mg (75%) of the title compound. ESI/APCI(+): 335 (M+H).

Workup

  1. customthe tube was sealed
  2. customirradiated in a microwave oven at 130° C. for 30 min
  3. customThe reaction mixture was partitioned between brine and ethyl acetate
  4. customthe phases were separated
  5. extractionthe water layer was extracted with ethyl acetate
  6. dry with materialThe combined organic layers were dried over magnesium sulphate
  7. concentrationconcentrated under reduced pressure
  8. customThe crude material was purified by flash chromatography on silica gel using a linear gradient of ethylacetate (10-80%) in heptane

Sources & evidence

ORD record
ord-e9775b0d16d9411f98e34e5d47be59fa
Source dataset
uspto-grants-2014_12
Patent number
US08906906B2

Reaction notes

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