Boron tribromide → HCID 22257963, compound

HRID 1611026Notes

Reaction equation

HRID 1611026 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:8]=[C:9]([S:13][C:14]2[C:22]3[C:21](=[O:23])[N:20]([CH3:24])[C:19](=[O:25])[N:18]([CH2:26][CH:27]([CH3:29])[CH3:28])[C:17]=3[S:16][C:15]=2[CH2:30][C:31]2[C:40]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[CH:34]=[CH:33][CH:32]=2)[CH:10]=[CH:11][CH:12]=1.C(=O)([O-])O.[Na+]>ClCCl>[CH3:30][CH2:15][CH2:14][CH:22]([CH3:21])[CH3:17].[OH:6][C:7]1[CH:8]=[C:9]([S:13][C:14]2[C:22]3[C:21](=[O:23])[N:20]([CH3:24])[C:19](=[O:25])[N:18]([CH2:26][CH:27]([CH3:28])[CH3:29])[C:17]=3[S:16][C:15]=2[CH2:30][C:31]2[C:40]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[CH:34]=[CH:33][CH:32]=2)[CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 22258033HCID 22258033, compound

Product 2

HCID 78922-MethylpentaneHCID 22257963HCID 22257963, compoundYield 99.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boron tribromide (1M solution in dichloromethane, 5.63 ml) was added to a stirred solution of 5-[(3-methoxyphenyl)thio]-3-methyl-1-(2-methylpropyl)-6-(1-naphthalenylmethyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (Example 26, 0.97 g) in anhydrous dichloromethane (50 ml) at 0° C. under nitrogen. After 1 hour, saturated sodium hydrogen carbonate solution (100 ml) was added and the mixture was extracted with ethyl acetate (2×100 ml). The organic extracts were dried over anhydrous magnesium sulfate, filtered and evaporated under reduced pressure. The residue was purified by column chromatography over silica, eluting with ethyl acetate:isohexane (3:2) and then recrystallised from ethyl acetate:isohexane to give the title compound (0.468 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate (2×100 ml)
  2. dry with materialThe organic extracts were dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customThe residue was purified by column chromatography over silica
  6. washeluting with ethyl acetate:isohexane (3:2)
  7. customrecrystallised from ethyl acetate

Sources & evidence

ORD record
ord-ad56be7f609742e3b845b9f0077aa815
Source dataset
uspto-grants-2006_01
Patent number
US06984644B2

Reaction notes

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