Benzo(B)Thiophene-2-Boronic Acid → 5-(benzo[b]thiophen-2-yl)-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine

HRID 731885Notes

Reaction equation

HRID 731885 reaction equation
I[C:2]1[C:10]2[C:9]([NH2:11])=[N:8][CH:7]=[N:6][C:5]=2[N:4]([CH3:12])[CH:3]=1.B(O)(O)[C:14]1[S:22][C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[S:22]1[C:14]([C:2]2[C:10]3[C:9]([NH2:11])=[N:8][CH:7]=[N:6][C:5]=3[N:4]([CH3:12])[CH:3]=2)=[CH:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:21]1=2

Participants

6

Reactant 3

HCID 2359Benzo(B)Thiophene-2-Boronic AcidHCID 62657Potassium Phosphate, TribasicHCID 594241805-Iodo-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine

Product 1

HCID 249052785-(benzo[b]thiophen-2-yl)-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 5-iodo-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine (5 mg, 0.018 mmol), benzo[b]thiophen-2-yl-2-boronic acid (16 mg, 0.091 mmol), K3PO4 (19.3 mg, 0.091 mmol) and Pd(PPh3)4 (12.5 mg, 0.011 mmol) in DMF (3 mL) was heated to 60° C. under an argon atmosphere. Reaction was concentrated in vacuo and purified by RP-HPLC (MeCN:H2O:0.1% TFA). ESI-MS (M+H)+ m/z calcd 281.1, found 281.3.

Workup

  1. customReaction
  2. concentrationwas concentrated in vacuo
  3. custompurified by RP-HPLC (MeCN:H2O:0.1% TFA)

Sources & evidence

ORD record
ord-600cc9cbe6d745ee97001c67bbc7c698
Source dataset
uspto-grants-2009_09
Patent number
US07585868B2

Reaction notes

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