Water → HCID 68647058, compound

HRID 1163029Notes

Reaction equation

HRID 1163029 reaction equation
[CH3:1][C:2]([CH3:22])([CH3:21])[CH2:3][N:4]([CH2:13][C:14]1[CH:19]=[CH:18][C:17](I)=[CH:16][CH:15]=1)[C:5]1[CH:10]=[CH:9][N:8]=[C:7]([C:11]#[N:12])[N:6]=1.[C:23]([Si:25]([CH3:28])([CH3:27])[CH3:26])#[CH:24].C(N(CC)CC)C.O>CN(C=O)C.[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>[CH3:1][C:2]([CH3:22])([CH3:21])[CH2:3][N:4]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:24]#[C:23][Si:25]([CH3:28])([CH3:27])[CH3:26])=[CH:16][CH:15]=1)[C:5]1[CH:10]=[CH:9][N:8]=[C:7]([C:11]#[N:12])[N:6]=1

Participants

8

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 44450361HCID 44450361, compound

Product 1

HCID 68647058HCID 68647058, compoundYield 330.6%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

At room temperature, a soln. of 4-[(2,2-Dimethyl-propyl)-(4-iodo-benzyl)-amino]-pyrimidine-2-carbonitrile (2 g, 4.9 mmoles) and ethynyl-trimethyl-silane (3.47 ml, 24.7 mmoles) in 20 ml of DMF is treated with triethylamine (2.6 ml, 14.8 mmoles), CuI (93 mg, 0.5 mmoles) and (Ph3P)2PdCl2 (0.2 g, 0.2 mmoles). The mixture is stirred at rt for overnight. Water is added and the organic layer is extracted with AcOEt, washed with brine, dried over magnesium sulfate and concentrated. The crude product is purified by silica gel column chromatography to give 6.1 g of desired 4-[(2,2-dimethyl-propyl)-(4-trimethylsilanylethynyl-benzyl)-amino]-pyrimidine-2-carbonitrile in 82% yield. Rf=0.52 (Hexane:AcOEt=1:1)

Workup

  1. customAt room temperature
  2. extractionthe organic layer is extracted with AcOEt
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe crude product is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e44ffe37f5c3418588e45f6ed9518a19
Source dataset
uspto-grants-2010_10
Patent number
US07820818B2

Reaction notes

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