Water → HCID 58961526, compound

HRID 2039736Notes

Reaction equation

HRID 2039736 reaction equation
Br[C:2]1[C:10]2[C:9]([Cl:11])=[N:8][CH:7]=[N:6][C:5]=2[NH:4][CH:3]=1.[Li]CCCC.[C:17]1([C:23](Cl)=[O:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.O>C1COCC1.CCOC(C)=O>[Cl:11][C:9]1[C:10]2[C:2]([C:23]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[O:24])=[CH:3][NH:4][C:5]=2[N:6]=[CH:7][N:8]=1

Participants

7

Reactant 4

HCID 962Water2×HCID 7412Benzoyl chlorideHCID 53807105-Bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidineHCID 178418339Butyllithium

Product 1

HCID 58961526HCID 58961526, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 5-bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine (1.47 g, 6.38 mmol) in THF (60 mL) at −78° C. under N2 was added n-BuLi (2.5 M in hexane, 5.74 mL, 14.36 mmol) dropwise. After completion of addition, the mixture was stirred at −78° C. for additional 40 min. PhCOCl (0.88 mL) was added and the reaction was stirred for an additional 1 hour. Water (1 mL) was added to quench the reaction. The reaction mixture was then poured into water (100 mL). EtOAc (200 mL) was added for extraction. The organic layer was separated, dried (Na2SO4), filtered and concentrated to a residue. The residue was dissolved into small amount of DCM and a little MeOH. It was loaded to silica gel column. The purification was down by eluent with 1/1 DCM/EtOAc. The (4-chloro-7H-pyrrolo[2,3-d]pyrimidin-5-yl)(phenyl)methanone was obtained as a white solid (0.49 g, 29%). 1H NMR (DMSO-d6, 400 MHz) 8.74 (s, 1H), 8.17 (s, 1H), 7.87 (m, 2H), 7.68 (m, 1H), 7.56 (m, 2H). LCMS [M+1]: 258.

Workup

  1. additionAfter completion of addition
  2. stirringthe reaction was stirred for an additional 1 hour
  3. customto quench
  4. customthe reaction
  5. customThe organic layer was separated
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated to a residue
  9. dissolutionThe residue was dissolved into small amount of DCM
  10. customThe purification

Sources & evidence

ORD record
ord-54506c055ff3492e97bb8d2a4bd8c5f1
Source dataset
uspto-grants-2013_11
Patent number
US08580803B2

Reaction notes

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