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

HRID 1405021Notes

Reaction equation

HRID 1405021 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]([OH:19])[CH:16]=[CH:17][CH:18]=1)#[CH:12].C(N(CC)CC)C>CN(C=O)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>[NH2:10][C:4]1[N:3]=[C:2]([Cl:1])[C:7]([C:12]#[C:11][C:13]2[CH:14]=[C:15]([OH:19])[CH:16]=[CH:17][CH:18]=2)=[C:6]([CH3:9])[N:5]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 139144m-EthynylphenolHCID 116447204-Chloro-5-iodo-6-methylpyrimidin-2-amine

Product 1

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

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

The title compound is synthesized according to general procedure GP2 starting from 1.5 g (5.7 mmol) 4-chloro-5-iodo-6-methyl-pyrimidin-2-ylamine (GP3) and 986 mg (8.4 mmol) 3-ethynyl-phenol using 106 mg (0.56 mmol) CuI, 390 mg (0.56 mmol) PdCl2(PPh3)2 and 8 mL (55 mmol) triethylamine in 12 mL dry DMF. For the work-up the solvent is removed in vacuo and the product is purified by chromatography on silica gel (DCM/MeOH gradient) and subsequently RP-HPLC (ACN/H2O gradient). Yield: 419 mg (29%).

Workup

  1. customFor the work-up the solvent is removed in vacuo
  2. customthe product is purified by chromatography on silica gel (DCM/MeOH gradient) and subsequently RP-HPLC (ACN/H2O gradient)

Sources & evidence

ORD record
ord-8f5f174b38794f44901ed39c5f7f576e
Source dataset
uspto-grants-2014_12
Patent number
US08916548B2

Reaction notes

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