Bromoform → Ethyl 6-bromo-2-[(2,3-difluorobenzyl)thio]-9H-purin-8-ylcarbamate

HRID 968235Notes

Reaction equation

HRID 968235 reaction equation
N[C:2]1[N:10]=[C:9]([S:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[C:14]=2[F:20])[N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([NH:21][C:22](=[O:26])[O:23][CH2:24][CH3:25])[NH:6]2.N(OCCC(C)C)=O.C(Br)(Br)[Br:36]>>[Br:36][C:2]1[N:10]=[C:9]([S:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[C:14]=2[F:20])[N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([NH:21][C:22](=[O:26])[O:23][CH2:24][CH3:25])[NH:6]2

Participants

4

Reactant 3

HCID 5558BromoformHCID 8053Isoamyl NitriteHCID 178473461HCID 178473461, compound

Product 1

HCID 178473456Ethyl 6-bromo-2-[(2,3-difluorobenzyl)thio]-9H-purin-8-ylcarbamate

Procedure

The product of example 5, step (d) (1 g) was dissolved in bromoform (14 ml) and iso-amyl nitrite (0.1 ml) and heated at 40° C. for 5 hr. The reaction mixture was then evaporated to dryness and purified by flash chromatography on silica gel with 20% ethyl acetate in dichloromethane, yielding the subtitled compound as a yellow solid (208 mg).

Workup

  1. customThe reaction mixture was then evaporated to dryness
  2. custompurified by flash chromatography on silica gel with 20% ethyl acetate in dichloromethane

Sources & evidence

ORD record
ord-bc2f4ae9228b4d139a0463af31a99e64
Source dataset
uspto-grants-2005_10
Patent number
US06958344B2

Reaction notes

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