Dimethylformamide → 3-(2-Amino-4-chloro-6-methyl-pyrimidin-5-ylethynyl)-phenol

HRID 1405029Notes

Reaction equation

HRID 1405029 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[CH:14]=[C:15]2[CH:21]=[CH:20]N[C:16]2=NC=1)#[CH:12].C(N(CC)CC)C.CN(C=[O:33])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>[NH2:10][C:4]1[N:3]=[C:2]([Cl:1])[C:7]([C:20]#[C:21][C:15]2[CH:14]=[C:13]([OH:33])[CH:11]=[CH:12][CH:16]=2)=[C:6]([CH3:9])[N:5]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 116447204-Chloro-5-iodo-6-methylpyrimidin-2-amineHCID 552879815-ethynyl-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 585133443-(2-Amino-4-chloro-6-methyl-pyrimidin-5-ylethynyl)-phenol

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalyst

Procedure

The title compound is synthesized according to general procedure GP2 starting from 500 mg (1.9 mmol) 4-chloro-5-iodo-6-methyl-pyrimidin-2-ylamine (GP3) and 396 mg (2.8 mmol) 5-ethynyl-1H-pyrrolo[2,3-b]pyridine (A-20) using 35 mg (0.19 mmol) CuI, 130 mg (0.19 mmol) PdCl2(PPh3)2 and 2.6 mL (19 mmol) triethylamine in 6 mL dry DMF. The product precipitates from the reaction mixture, is filtered off and washed with DMF. Yield: 436 mg (75%).

Workup

  1. customThe product precipitates from the reaction mixture
  2. filtrationis filtered off
  3. washwashed with DMF

Sources & evidence

ORD record
ord-9bb0f0c4419945a8b86f1db19323bb3f
Source dataset
uspto-grants-2014_12
Patent number
US08916548B2

Reaction notes

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