Iodine → 5-Bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine

HRID 882109Notes

Reaction equation

HRID 882109 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][NH:5][C:4]2=[N:8][CH:9]=[CH:10][C:3]=12.[Br:11]N1C(=O)CCC1=O.C(OCC)(=O)C.II>C(#N)C>[Br:11][C:10]1[C:3]2[C:2]([Cl:1])=[N:7][CH:6]=[N:5][C:4]=2[NH:8][CH:9]=1

Participants

6

Reactant 4

HCID 807IodineHCID 8857Ethyl AcetateHCID 67184N-bromobutanimideHCID 178418725HCID 178418725, compound

Product 1

HCID 53807105-Bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
40 °C

Procedure

To a magnetically stirred solution of 4-chloropyrrolo(2,3-d)pyrimidine (30.0 g, 195 mmol) in acetonitrile (300 mL) at 85° C. was added N-bromosuccinimide (34.8 g, 195 mmol) portion-wise during a period of 10 minutes and the reaction mixture was stirred at 40° C. for 1 hour, then at room temperature for another 30 minutes. The reaction progress was monitored by TLC using 30% ethyl acetate in petroleum ether with iodine and 254 nm UV light to visualize the spot. The reaction mixture was allowed to stand for 1 hour so that precipitation occurred completely. The resulting solid was filtered and washed with chilled water (250 mL), then dried under high vacuum to give 5-bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine as brown solid. LRMS (ESI) calc'd for C6H4BrClN3 [M+H]+, 232; found 232. 1H NMR (400 MHz, DMSO-D6,) δ: 12.98 (s, 1 H), 8.60 (s, 1H), 7.96 (d, J=2.4 Hz, 1H).

Workup

  1. waitat room temperature for another 30 minutes
  2. customto stand for 1 hour so that precipitation
  3. filtrationThe resulting solid was filtered
  4. washwashed with chilled water (250 mL)
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-459c277677444321bc484aeba9ad733f
Source dataset
uspto-grants-2015_03
Patent number
US08993756B2

Reaction notes

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