Ammonia → HCID 21062821, compound

HRID 1242806Notes

Reaction equation

HRID 1242806 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:15]3[CH:25]=[C:24]([CH2:26][CH3:27])[S:23][C:16]=3[N:17]=[C:18]([C:20](O)=[O:21])[N:19]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N1C=CN=C1)([N:30]1C=CN=C1)=O.N>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:15]3[CH:25]=[C:24]([CH2:26][CH3:27])[S:23][C:16]=3[N:17]=[C:18]([C:20](=[O:21])[NH2:30])[N:19]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 682631,1'-CarbonyldiimidazoleHCID 21939605HCID 21939605, compound

Product 1

HCID 21062821HCID 21062821, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-(4-tert-Butoxycarbonyl-piperazin-1-yl)-6-ethyl-thieno[2,3-d]pyrimidine-2-carboxylic acid (102.3 mg) was dissolved in tetrahydrofuran (0.50 mL) and 1,1′-carbonyl-diimidazole (42.3 mg) was added. The reaction was stirred at room temperature for 30 minutes and ammonia (0.5 M in dioxane, 1.57 mL) was added. The reaction was stirred at room temperature for 8 days and concentrated to dryness. The residue was purified on silica gel (0% to 10% ethyl acetate/hexane over 30 minutes) giving the desired product. Yield=47%, ES-MS: (M+H)+ 392.

Workup

  1. stirringThe reaction was stirred at room temperature for 8 days
  2. concentrationconcentrated to dryness
  3. customThe residue was purified on silica gel (0% to 10% ethyl acetate/hexane over 30 minutes)

Sources & evidence

ORD record
ord-b03401c565824544bff8a0fc28f8e41f
Source dataset
uspto-grants-2006_10
Patent number
US07115741B2

Reaction notes

Loading…