Triethyl phosphite → HCID 59649414, compound

HRID 709306Notes

Reaction equation

HRID 709306 reaction equation
Br[CH2:2][C:3]1[N:4]=[CH:5][C:6]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[N:7][CH:8]=1.[CH2:17]([O:19][P:20]([O:24]CC)[O:21][CH2:22][CH3:23])[CH3:18]>>[CH2:17]([O:19][P:20]([CH2:2][C:3]1[N:4]=[CH:5][C:6]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[N:7][CH:8]=1)([O:21][CH2:22][CH3:23])=[O:24])[CH3:18]

Participants

3

Reactant 2

HCID 31215Triethyl phosphiteHCID 45073740tert-Butyl (5-(bromomethyl)pyrazin-2-yl)carbamate

Product 1

HCID 59649414HCID 59649414, compoundYield 60%

Conditions

Temperature
140 °C

Procedure

tert-butyl 5-(bromomethyl)pyrazin-2-ylcarbamate (2.5 g, 8.71 mmol) and triethylphosphite (1.8 ml, 10.45 mmol) were placed in a 25 mL round bottom flask. A distillation apparatus was attached to collect the poisonous ethyl bromide formed during the reaction. The reaction mixture was heated to 140° C. for 30 minutes and then cooled to room temperature. The reaction mixture was purified by flash column chromatography (10% to 30% Ethyl acetate/Hexane) to afford title product (1.8 g, 60% yield). 1H NMR (600 MHz, CDCl3) δ 9.19 (s, 1H), 8.22 (t, J=1.8 Hz, 1H), 7.37 (s, 1H), 4.12-4.07 (m, 4H), 3.38 (s, 1H), 3.34 (s, 1H), 1.54 (s, 9H), 1.29 (t, J=7.2 Hz, 6H). MS m/z: 346 [M+1].

Workup

  1. customto collect the poisonous ethyl bromide
  2. customformed during the reaction
  3. temperaturecooled to room temperature
  4. customThe reaction mixture was purified by flash column chromatography (10% to 30% Ethyl acetate/Hexane)

Sources & evidence

ORD record
ord-f079e99dd06047d1aaffef0622de8719
Source dataset
uspto-grants-2015_11
Patent number
US09180127B2

Reaction notes

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