Phenyl isocyanate → HCID 11744026, compound

HRID 32639Notes

Reaction equation

HRID 32639 reaction equation
[C:1]1([N:7]=[C:8]=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:10][C:11]1[CH:12]=[C:13]([C:17]2[N:18]=[CH:19][N:20]([CH3:32])[C:21]=2[C:22]2[S:31][C:25]3[N:26]=[CH:27][N:28]=[C:29]([NH2:30])[C:24]=3[CH:23]=2)[CH:14]=[CH:15][CH:16]=1>C1COCC1>[NH2:30][C:29]1[C:24]2[CH:23]=[C:22]([C:21]3[N:20]([CH3:32])[CH:19]=[N:18][C:17]=3[C:13]3[CH:12]=[C:11]([NH:10][C:8]([NH:7][C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)=[O:9])[CH:16]=[CH:15][CH:14]=3)[S:31][C:25]=2[N:26]=[CH:27][N:28]=1

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 690543996-[4-(3-aminophenyl)-1-methyl-1H-imidazol-5-yl]thieno[2,3-d]pyrimidin-4-amine2×

Product 1

HCID 11744026HCID 11744026, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Phenyl isocyanate (28 mg) was added to a stirred suspension of 6-[4-(3-aminophenyl)-1-methyl-1H-imidazol-5-yl]thieno[2,3-d]pyrimidin-4-amine (Intermediate 110) (40 mg) in THF (6 mL) under an inert atmosphere. After 30 minutes methylethylenediamine-polystyrene (200 mg) was added, the reaction mixture filtered, filtrate loaded onto a MCX column washed with DCM/MeOH (1:1) then eluted with 5% triethylamine in DCM/MeOH (1:1) to give the title compound as a colourless solid (35 mg, 67%);

Workup

  1. filtrationthe reaction mixture filtered
  2. washwashed with DCM/MeOH (1:1)
  3. washthen eluted with 5% triethylamine in DCM/MeOH (1:1)

Sources & evidence

ORD record
ord-9d8cdc4c1eda458e9f671472a9e79bd1
Source dataset
uspto-grants-2008_09
Patent number
US07427616B2

Reaction notes

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