Pyridine → 2-(isopropylamino)-4-(5-(phenylamino)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidine-5-carbonitrile

HRID 40867Notes

Reaction equation

HRID 40867 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[C:16]([C:17]#[N:18])=[CH:15][N:14]=[C:13]([NH:19][CH:20]([CH3:22])[CH3:21])[N:12]=3)=[CH:9][N:8]([S:23]([C:26]3[CH:32]=[CH:31][C:29]([CH3:30])=[CH:28][CH:27]=3)(=[O:25])=[O:24])[C:5]2=[N:6][CH:7]=1.[C:33]1(B(O)O)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.N1C=CC=CC=1>C(Cl)Cl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH:20]([NH:19][C:13]1[N:12]=[C:11]([C:10]2[C:4]3[C:5](=[N:6][CH:7]=[C:2]([NH:1][C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[CH:3]=3)[N:8]([S:23]([C:26]3[CH:27]=[CH:28][C:29]([CH3:30])=[CH:31][CH:32]=3)(=[O:24])=[O:25])[CH:9]=2)[C:16]([C:17]#[N:18])=[CH:15][N:14]=1)([CH3:21])[CH3:22]

Participants

6

Reactant 3

HCID 1049PyridineHCID 66827Phenylboronic AcidHCID 686682684-(5-amino-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-2-(isopropylamino)pyrimidine-5-carbonitrile

Product 1

HCID 686678792-(isopropylamino)-4-(5-(phenylamino)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidine-5-carbonitrileYield 36%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

4-(5-amino-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-2-(isopropylamino)pyrimidine-5-carbonitrile (0.204 g, 0.455 mmol) in DCM (12 mL) was treated with phenylboronic acid (0.111 g, 0.910 mmol, 2.0 Eq), copper acetate (0.124 g, 0.682 mmol, 1.5 Eq), pyridine (0.074 mL, 0.910 mmol, 2.0 Eq) and 4 Angstrom molecular sieves (0.600 g) and the reaction was allowed to stir at room temperature for 16 hours. The reaction mixture was quenched with 4M Ammonia in MeOH (12 mL) and filtered through a plug of celite whilst washing through with further DCM/MeOH. The combined washes were evaporated to dryness and purified by column chromatography (ISCO Companion™, 12 g column, 0-100% EtOAc/Petroleum Ether) to give the title compound as a yellow solid (85 mg, 36%).

Workup

  1. customThe reaction mixture was quenched with 4M Ammonia in MeOH (12 mL)
  2. filtrationfiltered through a plug of celite
  3. washwhilst washing through with further DCM/MeOH
  4. customThe combined washes were evaporated to dryness
  5. custompurified by column chromatography (ISCO Companion™, 12 g column, 0-100% EtOAc/Petroleum Ether)

Sources & evidence

ORD record
ord-14400997e8ed475185fa46b5b443ac7d
Source dataset
uspto-grants-2013_09
Patent number
US08530489B2

Reaction notes

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