Boron tribromide → 4-[5-(4-Aminothieno[2,3-d]pyrimidin-6-yl)-1-methyl-1H-imidazol-4-yl]phenol

HRID 32638Notes

Reaction equation

HRID 32638 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:14]=[CH:15][N:16]([CH3:28])[C:17]=2[C:18]2[S:27][C:21]3[N:22]=[CH:23][N:24]=[C:25]([NH2:26])[C:20]=3[CH:19]=2)=[CH:9][CH:8]=1>C(Cl)Cl>[NH2:26][C:25]1[C:20]2[CH:19]=[C:18]([C:17]3[N:16]([CH3:28])[CH:15]=[N:14][C:13]=3[C:10]3[CH:11]=[CH:12][C:7]([OH:6])=[CH:8][CH:9]=3)[S:27][C:21]=2[N:22]=[CH:23][N:24]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 691973206-[4-(4-Methoxyphenyl)-1-methyl-1H-imidazol-5-yl]thieno[2,3-d]pyrimidin-4-amine2×

Product 1

HCID 102456254-[5-(4-Aminothieno[2,3-d]pyrimidin-6-yl)-1-methyl-1H-imidazol-4-yl]phenolYield 71.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boron tribromide (1.0M in DCM) (10.1 mL) was added dropwise to 6-[4-(4-methoxyphenyl)-1-methyl-1H-imidazol-5-yl]thieno[2,3-d]pyrimidin-4-amine (Intermediate 107) (0.91 g) in DCM (20 mL) then stirred for 5 days at ambient temperature. The reaction mixture was concentrated in vacuo and the residue partitioned between DCM and water. The aqueous layer was separated and extracted with DCM (3×20 mL), the aqueous layer was then adjusted to pH 9 with concentrated aqueous NH3, the resultant solid filtered and dried in vacuo to give the title compound as a brown solid (623 mg, 71%);

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue partitioned between DCM and water
  3. customThe aqueous layer was separated
  4. extractionextracted with DCM (3×20 mL)
  5. filtrationthe resultant solid filtered
  6. customdried in vacuo

Sources & evidence

ORD record
ord-00df8c269c7340d5b8691fb31c0aa138
Source dataset
uspto-grants-2008_09
Patent number
US07427616B2

Reaction notes

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