Triethylamine → HCID 58513556, compound

HRID 1405030Notes

Reaction equation

HRID 1405030 reaction equation
[Cl:1][C:2]1[C:7](I)=[C:6]([CH3:9])[N:5]=[C:4]([NH2:10])[N:3]=1.[C:11]([C:13]1[N:17]([CH3:18])[CH:16]=[N:15][CH:14]=1)#[CH:12].C(N(CC)CC)C>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:1][C:2]1[C:7]([C:12]#[C:11][C:13]2[N:17]([CH3:18])[CH:16]=[N:15][CH:14]=2)=[C:6]([CH3:9])[N:5]=[C:4]([NH2:10])[N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 33331065-Ethynyl-1-methyl-1H-imidazoleHCID 116447204-Chloro-5-iodo-6-methylpyrimidin-2-amine

Product 1

HCID 58513556HCID 58513556, compound

Reagents, catalysts & solvents 1

HCID 178418476HCID 178418476, compoundCatalyst

Procedure

The title compound is synthesized according to general procedure GP2 starting from 1.4 g (5.3 mmol) 4-chloro-5-iodo-6-methyl-pyrimidin-2-ylamine (A-3) and 900 mg (8.5 mmol) 5-ethynyl-1-methyl-1H-imidazole using 10 mg (0.05 mmol) CuI, 112 mg (0.03 mmol) PdCl2(PPh3)2, 5.3 mL (5.3 mmol) of 9-methoxy-9-BBN and 1.3 mL (9.5 mmol) triethylamine in 125 mL degassed and dry acetonitril. The product precipitates from the reaction mixture and is filtered off. Yield: 780 mg (54%).

Workup

  1. customdegassed
  2. customThe product precipitates from the reaction mixture
  3. filtrationis filtered off

Sources & evidence

ORD record
ord-1cab04a17bb944e2a9dba70758caa9a3
Source dataset
uspto-grants-2014_12
Patent number
US08916548B2

Reaction notes

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