1-Butanol → 6-(4-Hydroxyphenyl)-1-(2-morpholinoethyl)-1H-imidazo[4,5-B]pyrazin-2(3H)-one

HRID 1014708Notes

Reaction equation

HRID 1014708 reaction equation
Br[C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[C:5]([NH2:17])=[N:4][CH:3]=1.BrC1N=[C:21](N)[C:22](N)=NC=1.[O:27]1CCN(CCN)C[CH2:28]1.C(N(C(C)C)CC)(C)C.[CH2:45]([OH:49])[CH2:46][CH2:47][CH3:48]>>[OH:49][C:45]1[CH:22]=[CH:21][C:48]([C:2]2[N:7]=[C:6]3[N:8]([CH2:9][CH2:10][N:11]4[CH2:16][CH2:15][O:14][CH2:13][CH2:12]4)[C:28](=[O:27])[NH:17][C:5]3=[N:4][CH:3]=2)=[CH:47][CH:46]=1

Participants

6

Reactant 5

HCID 2631-ButanolHCID 81531DiisopropylethylamineHCID 4082852-MorpholinoethylamineHCID 27718575-Bromopyrazine-2,3-diamineHCID 717297036-Bromo-N2-(2-morpholinoethyl)pyrazine-2,3-diamine

Product 1

HCID 1358710166-(4-Hydroxyphenyl)-1-(2-morpholinoethyl)-1H-imidazo[4,5-B]pyrazin-2(3H)-oneYield 88%

Procedure

6-Bromo-N2-(2-morpholinoethyl)pyrazine-2,3-diamine. In a sealed tube, a solution of 5-bromopyrazine-2,3-diamine (5.0 g, 19.7 mmol), 2-morpholinoethanamine (5.14 g, 39.5 mmol), diisopropylethylamine (6.9 mL, 39.5 mmol) in n-butanol (100 mL) was heated at 120° C. for 17 h. The volatiles were removed under reduced pressure. The residue was taken up in hexanes and diethylether and sonicated. The resulting precipitate was collected by filtration to provide the title compound (5.23 g, 88%). MS (ESI) m/z 304.2 [M+1]+.

Workup

  1. customThe volatiles were removed under reduced pressure
  2. customdiethylether and sonicated
  3. filtrationThe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-88f1586c793648dca07a1937c8ae7bb4
Source dataset
uspto-grants-2011_07
Patent number
US07981893B2

Reaction notes

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