Ethyl Acetate → HCID 178450821, compound

HRID 2169434Notes

Reaction equation

HRID 2169434 reaction equation
C(O)(=O)C.[N:5]1([C:14]2([CH2:19][C:20]([NH2:22])=[NH:21])[CH2:18][CH2:17][CH2:16][CH2:15]2)[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[CH:7]=[CH:6]1.[C:23]([O:27][C:28](=[O:43])/[C:29](/O)=[C:30](\[O:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)/[C:31](O)=[O:32])([CH3:26])([CH3:25])[CH3:24].C[O-].[Na+].C(OCC)(=O)C>CO>[C:23]([O:27][C:28]([C:29]1[C:30]([O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[C:31]([OH:32])[N:22]=[C:20]([CH2:19][C:14]2([N:5]3[C:9]4=[N:10][CH:11]=[CH:12][CH:13]=[C:8]4[CH:7]=[CH:6]3)[CH2:18][CH2:17][CH2:16][CH2:15]2)[N:21]=1)=[O:43])([CH3:26])([CH3:24])[CH3:25]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 10942334Sodium MethoxideHCID 86725882(E)-2-benzyloxy-3-hydroxy-but-2-enedioic acid 4-tert-butyl esterHCID 86726064Acetic acid;2-(1-pyrrolo[2,3-b]pyridin-1-ylcyclopentyl)ethanimidamide

Product 1

HCID 178450821HCID 178450821, compoundYield 75.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a stirred solution of 2-(1-pyrrolo[2,3-b]pyridin-1-yl-cyclopentyl)-acetamidine; compound with acetic acid (402) (800 mg, 2.65 mmol) and (E)-3-benzyloxy-2-hydroxy-4-oxo-pent-2-enoic acid tert-butyl ester (4) (978 mg, 3.18 mmol) in methanol (80 mL) was added sodium methoxide solution (25% in methanol) (1.7 mL, 7.94 mmol) at 0° C. The reaction mixture was allowed to warm slowly to room temperature and was stirred for 16 h (TLC, ethyl acetate, Rf=0.3). After completion of the reaction, methanol was evaporated to get a crude product which was purified by Combi-Flash column (eluted at 60-70% ethyl acetate in hexane) to get 5-benzyloxy-6-hydroxy-2-(1-pyrrolo[2,3-b]pyridin-1-yl-cyclopentylmethyl)-pyrimidine-4-carboxylic acid tert-butyl ester (403) (1 g, 75%) as a light yellow solid.

Workup

  1. customwas evaporated
  2. customto get a crude product which
  3. customwas purified by Combi-Flash column (eluted at 60-70% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-be57e476fb8a44d0b36bd91b73511355
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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