Water → 6-[1-(1-Methylpyrrolidin-3-yl)-4-phenyl-1H-imidazol-5-yl]thieno[2,3-d]pyrimidin-4-amine

HRID 32627Notes

Reaction equation

HRID 32627 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH2:7][C:8]1[C:9]2[CH:16]=[C:15]([C:17]3[N:21]([CH:22]4[CH2:26][CH2:25][N:24]([C:27](OC(C)(C)C)=O)[CH2:23]4)[CH:20]=[N:19][C:18]=3[C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[S:14][C:10]=2[N:11]=[CH:12][N:13]=1.O>C1COCC1.C(O)(C(F)(F)F)=O>[CH3:27][N:24]1[CH2:25][CH2:26][CH:22]([N:21]2[C:17]([C:15]3[S:14][C:10]4[N:11]=[CH:12][N:13]=[C:8]([NH2:7])[C:9]=4[CH:16]=3)=[C:18]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[N:19]=[CH:20]2)[CH2:23]1

Participants

6

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 69197495tert-butyl 3-[5-(4-aminothieno[2,3-d]pyrimidin-6-yl)-4-phenyl-1H-imidazol-1-yl]pyrrolidine-1-carboxylate2×

Product 1

HCID 100224226-[1-(1-Methylpyrrolidin-3-yl)-4-phenyl-1H-imidazol-5-yl]thieno[2,3-d]pyrimidin-4-amineYield 28%

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of lithium aluminium hydride in THF (1M, 0.1 mL), THF (2 mL) and tert-butyl 3-[5-(4-aminothieno[2,3-d]pyrimidin-6-yl)-4-phenyl-1H-imidazol-1-yl]pyrrolidine-1-carboxylate (intermediate 102) (31 mg) was refluxed for 4 hours under an inert atmosphere. After addition of water and TFA (1 drop), the mixture was evaporated and the residue was purified by preparative RPHPLC (eluting with a gradient of MeCN and water containing 0.1% TFA) to afford the title compound as a colourless solid (5 mg, 28%).

Workup

  1. temperaturewas refluxed for 4 hours under an inert atmosphere
  2. customthe mixture was evaporated
  3. customthe residue was purified by preparative RPHPLC (
  4. washeluting with a gradient of MeCN and water containing 0.1% TFA)

Sources & evidence

ORD record
ord-a7219b19809e4c6baa966b053d79b2d4
Source dataset
uspto-grants-2008_09
Patent number
US07427616B2

Reaction notes

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