Triethylamine → HCID 58626126, compound

HRID 1161676Notes

Reaction equation

HRID 1161676 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2[N:16]=[C:15](Cl)[CH:14]=[C:13]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[N:12]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].C(N(CC)CC)C.[C:31]1([C:37]#[CH:38])[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>CN(C)C=O.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu](I)I>[Cl:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2[N:12]=[C:13]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:14]=[C:15]([C:38]#[C:37][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[N:16]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]

Participants

8

Reactant 3

HCID 8471TriethylamineHCID 10821PhenylacetyleneHCID 58626069HCID 58626069, compound

Product 1

HCID 58626126HCID 58626126, compound

Reagents, catalysts & solvents 4

HCID 83717Copper iodideCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of compound (3-chloro-4-methoxy-phenyl)-(4-chloro-6-phenyl-pyrimidin-2-yl)-amine (0.4 g, 1.15 mmol), (PPh3)4Pd (53 mg, 0.05 mmol), copper iodide (11 mg, 0.06 mmol) and triethylamine (0.93 g, 9.23 mmol) in dimethylformamide (10 mL) was stirred at 80° C. for 0.5 hour under nitrogen atmosphere. The mixture was cooled to temperature in the range of 20-40° C. and phenylacetylene (0.24 g, 2.30 mmol) was added to it. The mixture was stirred at 80° C. for 12 hours under nitrogen atmosphere. The mixture was cooled to temperature in the range of 20-40° C., diluted with water (20 mL) and extracted with ethyl acetate (3×15 mL). The organic layers were collected, combined, washed with water (10 mL), dried over anhydrous sodium sulphate and concentrated under vacuum. The residue was purified by column chromatography using ethyl acetate-petroleum ether to give the desired product.

Workup

  1. additionwas added to it
  2. stirringThe mixture was stirred at 80° C. for 12 hours under nitrogen atmosphere
  3. temperatureThe mixture was cooled to temperature in the range of 20-40° C.
  4. extractionextracted with ethyl acetate (3×15 mL)
  5. customThe organic layers were collected
  6. washwashed with water (10 mL)
  7. dry with materialdried over anhydrous sodium sulphate
  8. concentrationconcentrated under vacuum
  9. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-a42188993af44794b85f99cb82def84d
Source dataset
uspto-grants-2010_10
Patent number
US07820654B2

Reaction notes

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