Sodium t-butoxide → 5-((1S,2S)-2-(3-methoxyphenyl)cyclopropyl)-7,7-dimethyl-5H-pyrrolo[2,3-b]pyrazin-6(7H)-one

HRID 707385Notes

Reaction equation

HRID 707385 reaction equation
Cl[C:2]1[C:3]([C:8]([CH3:24])([CH3:23])[C:9]([NH:11][CH:12]2[CH2:14][CH:13]2[C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=2)=[O:10])=[N:4][CH:5]=[CH:6][N:7]=1.CC(C)([O-])C.[Na+].COC1C=C([C@H]2C[C@@H]2N2C3=NC=CN=C3C(C)(C)C2=O)C=CC=1>C1COCC1>[CH3:22][O:21][C:17]1[CH:16]=[C:15]([C@@H:13]2[CH2:14][C@@H:12]2[N:11]2[C:2]3=[N:7][CH:6]=[CH:5][N:4]=[C:3]3[C:8]([CH3:24])([CH3:23])[C:9]2=[O:10])[CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 23676156Sodium t-butoxideHCID 866942442-(3-chloropyrazin-2-yl)-N-(2-(3-methoxyphenyl)cyclopropyl)-2-methylpropanamideHCID 866942465-((1S,2R)-2-(3-methoxyphenyl)cyclopropyl)-7,7-dimethyl-5H-pyrrolo[2,3-b]pyrazin-6(7H)-one

Product 1

HCID 866942455-((1S,2S)-2-(3-methoxyphenyl)cyclopropyl)-7,7-dimethyl-5H-pyrrolo[2,3-b]pyrazin-6(7H)-oneYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-(3-chloropyrazin-2-yl)-N-(2-(3-methoxyphenyl)cyclopropyl)-2-methylpropanamide (0.183 g, 0.529 mmol), sodium tert-butoxide (Aldrich, 0.102 g, 1.058 mmol) in THF was stirred at room temperature overnight. Reaction mixture was directly loaded onto a Biotage samplet. Purification (0-100% EtOAc/hexane) produced mixture of products 5-((1S,2R)-2-(3-methoxyphenyl)cyclopropyl)-7,7-dimethyl-5H-pyrrolo[2,3-b]pyrazin-6(7H)-one and 5-((1S,2S)-2-(3-methoxyphenyl)cyclopropyl)-7,7-dimethyl-5H-pyrrolo[2,3-b]pyrazin-6(7H)-one (0.111 g, 0.359 mmol, 68% yield). M+1: 310.0. 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 1.45 (d, J=1.90 Hz, 6 H) 1.54-1.63 (m, 1 H) 1.66-1.75 (m, 1 H) 2.62 (ddd, J=9.87, 6.72, 3.58 Hz, 1 H) 2.93-3.06 (m, 1 H) 3.82 (s, 3 H) 6.73-6.83 (m, 1 H) 6.86-6.97 (m, 2 H) 7.16-7.31 (m, 1 H) 8.11 (s, 2 H).

Workup

  1. customReaction mixture
  2. customPurification (0-100% EtOAc/hexane)
  3. customproduced

Sources & evidence

ORD record
ord-56a1e0007b4a449881bf09e9978134e1
Source dataset
uspto-grants-2015_11
Patent number
US09174992B2

Reaction notes

Loading…