Water → HCID 18362952, compound

HRID 1276695Notes

Reaction equation

HRID 1276695 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:8]=[C:9]([S:13][C:14]2[N:15]([CH2:30][C:31]3[C:40]4[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=4)[CH:34]=[CH:33][CH:32]=3)[CH:16]=[C:17]3[C:22]=2[C:21](=[O:23])[N:20]([CH3:24])[C:19](=[O:25])[N:18]3[CH2:26][CH:27]([CH3:29])[CH3:28])[CH:10]=[CH:11][CH:12]=1.O>ClCCl>[OH:6][C:7]1[CH:8]=[C:9]([S:13][C:14]2[N:15]([CH2:30][C:31]3[C:40]4[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=4)[CH:34]=[CH:33][CH:32]=3)[CH:16]=[C:17]3[C:22]=2[C:21](=[O:23])[N:20]([CH3:24])[C:19](=[O:25])[N:18]3[CH2:26][CH:27]([CH3:28])[CH3:29])[CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 18362927HCID 18362927, compound2×

Product 1

HCID 18362952HCID 18362952, compoundYield 61.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of boron tribromide in dichloromethane (1M, 3 ml) was added to a solution of 5-([3-methoxyphenyl]thio)-3-methyl-1-(2-methylpropyl)-6-(1-naphthalenylmethyl)-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione (200 mg) (compound of Example 23) in dichloromethane (20 ml) at ambient temperature. After 6 hours, water (10 ml) was added carefully and the reaction mixture was partitioned between dichloromethane and brine. The organic phase was dried over magnesium sulphate, filtered and evaporated in vacuo. Purification by chromatography on silica gel, eluting with isohexane/ethyl acetate (2:1 to 1:1) followed by recrystallisation from isohexane/ethyl acetate (3:1), gave the title compound (120 mg).

Workup

  1. customthe reaction mixture was partitioned between dichloromethane and brine
  2. dry with materialThe organic phase was dried over magnesium sulphate
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customPurification by chromatography on silica gel
  6. washeluting with isohexane/ethyl acetate (2:1 to 1:1)
  7. customfollowed by recrystallisation from isohexane/ethyl acetate (3:1)

Sources & evidence

ORD record
ord-734eae46ba87461e88656fe63ae0c623
Source dataset
uspto-grants-2000_12
Patent number
US06166206

Reaction notes

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