Triethylamine → HCID 86712738, compound

HRID 1779111Notes

Reaction equation

HRID 1779111 reaction equation
[NH2:1][C:2](=[O:39])[CH2:3][C:4]1[CH:38]=[CH:37][CH:36]=[CH:35][C:5]=1[CH2:6][CH2:7]C1C(C(F)(F)F)=CN=C(NC2C=CC(C(NC(=O)OC(C)(C)C)C)=CC=2)N=1.[Cl:40][C:41]1[N:46]=[C:45](Cl)[C:44]([Cl:48])=[CH:43][N:42]=1.CCN(CC)CC>O1CCOCC1.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:40][C:41]1[N:46]=[C:45]([C:7]#[C:6][C:5]2[CH:35]=[CH:36][CH:37]=[CH:38][C:4]=2[CH2:3][C:2]([NH2:1])=[O:39])[C:44]([Cl:48])=[CH:43][N:42]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 2372592,4,5-TrichloropyrimidineHCID 86712739HCID 86712739, compound

Product 1

HCID 86712738HCID 86712738, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 18 (0.75 g, 4.7 mmol) and 2,4,5-trichloropyrimidine (0.70 mL, 6.1 mmol) in 1,4-dioxane (10 mL) and Et3N (2.6 mL, 19 mmol) containing CuI (0.018 g, 0.094 mmol) was added PdCl2(PPh3)2 (0.033 g, 0.047 mmol). The reaction mixture was heated at 70° C. for 2 hours under a nitrogen atmosphere. The solvent was removed in vacuo and the residue was diluted with 20% diethyl ether in cyclohexane. The precipitate was filtered, washed with water and dried in vacuo to give the title compound (A138) as a light brown solid (1.22 g, 85%). LCMS-C: rt 4.88 min; m/z 306 [M+H]+.

Workup

  1. customThe solvent was removed in vacuo
  2. additionthe residue was diluted with 20% diethyl ether in cyclohexane
  3. filtrationThe precipitate was filtered
  4. washwashed with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-8cec7fe60cd24727bd81dacc96c8315a
Source dataset
uspto-grants-2016_02
Patent number
US09266864B2

Reaction notes

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