Tetrahydrofuran → HCID 136373242, compound

HRID 1014731Notes

Reaction equation

[C:1](OC(N1CCCC1CNC1C(N)=NC=C(Br)N=1)=O)(C)(C)[CH3:2].Br[C:24]1[N:29]=[C:28]2[N:30]([CH2:34][CH:35]3[CH2:39][CH2:38][CH2:37][N:36]3C(OC(C)(C)C)=O)[C:31](=[O:33])[NH:32][C:27]2=[N:26][CH:25]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[O:59]1[CH2:63][CH2:62][CH2:61][CH2:60]1>>[OH:59][C:63]1[CH:62]=[CH:61][C:60]([C:24]2[N:29]=[C:28]3[N:30]([CH2:34][CH:35]4[CH2:39][CH2:38][CH2:37][NH:36]4)[C:31](=[O:33])[NH:32][C:27]3=[N:26][CH:25]=2)=[CH:2][CH:1]=1

Participants

Reactant 3

HCID 8028Tetrahydrofuran

HCID 682631,1'-Carbonyldiimidazole

HCID 86626411HCID 86626411, compound

Product 1

HCID 136373242HCID 136373242, compoundYield 80%

Conditions

Temperature: 120 °C

Procedure

tert-Butyl 2-((6-bromo-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyrazin-1-yl)methyl)pyrrolidine-1-carboxylate tert-Butyl 2-((3-amino-6-bromopyrazin-2-ylamino)methyl)pyrrolidine-1-carboxylate (2.0 g., 5.4 mmol), 1,1′-carbonyldiimidazole (1.75 g., 10.80 mmol), and tetrahydrofuran (7 mL) were combined in a sealed tube and heated to 120° C. overnight. The solvent was removed and the crude purified using silica gel chromatography (20% hexane in ethyl acetate) to yield the title compound (1.73 g., 80% yield). MS (ESI) m/z 398 [M]+, 400 [M+2]+.

Workup

customThe solvent was removed
customthe crude purified

Sources & evidence

ORD record: ord-39557a5a70814af39277195fd1f16264
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07981893B2

Reaction notes

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