Diisopropylethylamine → HCID 86626400, compound

HRID 1014712Notes

Reaction equation

HRID 1014712 reaction equation
[Br:1][C:2]1[N:7]=[C:6]2[N:8]([CH2:12][CH2:13][CH:14]3[CH2:19][CH2:18][O:17][C:16]([CH3:21])([CH3:20])[CH2:15]3)C(=O)[NH:10][C:5]2=[N:4][CH:3]=1.BrC1C(N)=NC=C(Br)N=1.Cl.CC1(C)CC(CCN)CCO1.C(N(C(C)C)CC)(C)C>CS(C)=O>[Br:1][C:2]1[N:7]=[C:6]([NH:8][CH2:12][CH2:13][CH:14]2[CH2:19][CH2:18][O:17][C:16]([CH3:20])([CH3:21])[CH2:15]2)[C:5]([NH2:10])=[N:4][CH:3]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 6200042-Amino-3,5-dibromopyrazineHCID 44660077HCID 44660077, compoundHCID 86626401HCID 86626401, compound

Product 1

HCID 86626400HCID 86626400, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

6-Bromo-1-(2-(2,2-dimethyltetrahydro-2H-pyran-4-yl)ethyl)-1H-imidazo[4,5-b]pyrazin-2(3H)-one. 3,5-Dibromopyrazin-2-amine (161 mg, 0.6 mmol), 2-(2,2-dimethyl-tetrahydro-pyran-4-yl)-ethylamine hydrochloride (100 mg, 0.5 mmol), diisopropylethylamine (0.5 mL), and dimethylsulfoxide (2 mL) were heated in a Biotage Emrys Optimizer microwave reactor to 150° C. for 2 h to give crude 6-bromo-N2-(2-(2,2-dimethyltetrahydro-2H-pyran-4-yl)ethyl)pyrazine-2,3-diamine. MS (ESI) m/z 329.5, 331.5 [M+1]+. 1,1′-Carbonyldiimidazole (194 mg, 1.2 mmol) was added to the reaction mixture and then heated again in a Biotage Emrys Optimizer microwave reactor to 150° C. for 10 min. The product was purified by reverse-phase semi-preparatory HPLC (10-70% acetonitrile+0.1% TFA in H2O+0.1% TFA, over 30 min). Product containing fractions were concentrated and then triturated with ether to give a white solid (90 mg, 42% yield over two steps). MS (ESI) m/z 355.4 [M]+, 357.4 [M+2]+.

Sources & evidence

ORD record
ord-1e8b1fb746b14f19bc842d4722448637
Source dataset
uspto-grants-2011_07
Patent number
US07981893B2

Reaction notes

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