Sodium Carbonate → 4-chloro-7-methyl-5-(3-biphenyl)-7H-pyrrolo[2,3-d]pyrimidine

HRID 238030Notes

Reaction equation

HRID 238030 reaction equation
[Cl:1][C:2]1[C:3]2[C:10](I)=[CH:9][N:8]([CH3:12])[C:4]=2[N:5]=[CH:6][N:7]=1.[C:13]1([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:18]=[CH:17][CH:16]=[C:15](B(O)O)[CH:14]=1.C([O-])([O-])=O.[Na+].[Na+]>C1COCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:12][N:8]1[C:4]2[N:5]=[CH:6][N:7]=[C:2]([Cl:1])[C:3]=2[C:10]([C:17]2[CH:18]=[C:13]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:14]=[CH:15][CH:16]=2)=[CH:9]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2734315(3-Phenylphenyl)boronic acidHCID 426094624-chloro-5-iodo-7-methyl-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 249051994-chloro-7-methyl-5-(3-biphenyl)-7H-pyrrolo[2,3-d]pyrimidineYield 28%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-chloro-5-iodo-7-methyl-7H-pyrrolo[2,3-d]pyrimidine (10 mg, 0.034 mmol), 3-biphenyl-boronic acid (7.4 mg, 0.038 mmol), Na2CO3 (36.1 mg, 0.34 mmol) and PdCl2(dppf) (1.4 mg, 0.0017 mmol) in THF (10 mL) was heated to reflux overnight under an argon atmosphere. Reaction was concentrated in vacuo and purified by RP-HPLC (MeCN:H2O:0.1% TFA) to yield ZK103 (3 mg, 28% yield). ESI-MS (M+H)+ m/z calcd 320.1, found 320.0.

Workup

  1. temperatureto reflux overnight under an argon atmosphere
  2. customReaction
  3. concentrationwas concentrated in vacuo
  4. custompurified by RP-HPLC (MeCN:H2O:0.1% TFA)

Sources & evidence

ORD record
ord-a54222baee56460baf77bb553f690e8b
Source dataset
uspto-grants-2014_02
Patent number
US08642604B2

Reaction notes

Loading…