HCID 86692151, compound → HCID 56948863, compound

HRID 527927Notes

Reaction equation

HRID 527927 reaction equation
[N:1]1[C:6]2[NH:7][CH:8]=[CH:9][C:5]=2[C:4]([N:10]2[CH2:14][CH2:13][C@@H:12]([N:15]([CH3:23])[C:16]3[N:21]=[CH:20][C:19](Br)=[CH:18][N:17]=3)[CH2:11]2)=[N:3][CH:2]=1.[C:24]([Zn]C#N)#[N:25]>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>[N:1]1[C:6]2[NH:7][CH:8]=[CH:9][C:5]=2[C:4]([N:10]2[CH2:14][CH2:13][C@@H:12]([N:15]([CH3:23])[C:16]3[N:21]=[CH:20][C:19]([C:24]#[N:25])=[CH:18][N:17]=3)[CH2:11]2)=[N:3][CH:2]=1

Participants

5

Reactant 2

HCID 86692151HCID 86692151, compoundHCID 178514179HCID 178514179, compound

Product 1

HCID 56948863HCID 56948863, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of (R)—N-(1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)pyrrolidin-3-yl)-5-bromo-N-methylpyrimidin-2-amine (50.0 mg, 0.134 mmol), dicyanozinc (15.7 mg, 0.134 mmol) and tetrakis(triphenylphosphine)palladium (15.4 mg, 0.0134 mmol) in 5 mL of DMF was stirred at 120° C. for 40 min in an Initator™ Biotage microwave reactor. The reaction mixture was partitioned between 15 mL of water and 20 mL of ethyl acetate. The organic layer was washed by brine, dried, concentrated and the residue was purified by preparative TLC to afford the title compound. MS (m/z): 321 (M+H)+.

Workup

  1. customThe reaction mixture was partitioned between 15 mL of water and 20 mL of ethyl acetate
  2. washThe organic layer was washed by brine
  3. customdried
  4. concentrationconcentrated
  5. customthe residue was purified by preparative TLC

Sources & evidence

ORD record
ord-65179777509846bfa85db182ae22e9e0
Source dataset
uspto-grants-2016_05
Patent number
US09346810B2

Reaction notes

Loading…