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Triethylamine → HCID 57714144, compound

HRID 1984240
Notes
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Reaction equation

HRID 1984240 reaction equation
Br[C:2]1[C:3]([NH:10][CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=[N:4][C:5]([C:8]#[N:9])=[N:6][CH:7]=1.[Cl:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][C:27]#[CH:28])=[CH:21][CH:20]=1.C(N(CC)CC)C.CCOC(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>[Cl:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][C:27]#[C:28][C:2]2[C:3]([NH:10][CH:11]3[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]3)=[N:4][C:5]([C:8]#[N:9])=[N:6][CH:7]=2)=[CH:21][CH:20]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 107498961-(Chloromethyl)-4-(2-propyn-1-yloxy)benzeneHCID 17968181HCID 17968181, compound

Product 1

HCID 57714144HCID 57714144, compoundYield 21%

Reagents, catalysts & solvents 3

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

Conditions

Temperature
65 °C

Procedure

5-Bromo-4-cyclohexylamino-pyrimidine-2-carbonitrile (0.19 mmol) and chloromethyl-4-prop-2-ynyloxy-benzene (0.22 mmol) in DMF (5 ml) are treated with triethylamine (0.56 mmol), copper (I) iodide (0.019 mmol), and dichlorobis(triphenylphosphine)palladium(II) (0.0093 mmol) at room temperature. The mixture is stirred for 2 h at 65° C., poured into an ice water, extracted with AcOEt. The organic layer is washed with brine, dried over magnesium sulfate and concentrated. The crude product is purified by silica gel column chromatography to give the product in 21% yield. Rf=0.75 (n-hexanes:AcOEt=1:2). 1H-NMR (400 MHz, CDCl3) δ 1.02-1.48 (m, 5H), 1.57-1.78 (m, 3H), 1.80-1.98 (m. 2H), 3.94-4.04 (m, 1H), 4.61(s, 2H), 5.03 (s, 2H), 5.38 (d, 1H), 7.04 (d, 2H), 7.41 (d, 2H), 8.21 (s, 1H).

Workup

  1. extractionextracted with AcOEt
  2. washThe organic layer is washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe crude product is purified by silica gel column chromatography
  6. customto give the product in 21% yield

Sources & evidence

ORD record
ord-e8507f8f34bd45db953ad8f2c46b9da9
Source dataset
uspto-grants-2009_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07544688B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes