Ethyl Acetate → HCID 86591412, compound

HRID 1063264Notes

Reaction equation

HRID 1063264 reaction equation
[Br:1][C:2]1[N:3]=[C:4]([CH2:16][CH3:17])[C:5]([NH:10][C@H:11]([CH2:14][CH3:15])[CH2:12][OH:13])=[N:6][C:7]=1[CH2:8][CH3:9].[C:18](OCC)(=O)C>CCCCCCC>[Br:1][C:2]1[N:3]=[C:4]([CH2:16][CH3:17])[C:5]([NH:10][C@@H:11]([CH2:12][O:13][CH3:18])[CH2:14][CH3:15])=[N:6][C:7]=1[CH2:8][CH3:9]

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 86591413HCID 86591413, compound

Product 1

HCID 86591412HCID 86591412, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Procedure

Following the general procedure of Example 13 Step 3 and making non-critical variations but substituting (2S)-2-[(5-bromo-3,6-diethylpyrazin-2-yl)amino]butan-1-ol with (2R)-2-[(5-bromo-3,6-diethylpyrazin-2-yl)amino]butan-1-ol (Example 12 Step 2) (353 mg, 1.17 mmol) gave 154 mg (42%) of 5-bromo-3,6-diethyl-N-[(1R)-1-(methoxymethyl)propyl]pyrazin-2-amine as a yellow oil after Biotage MPLC (40 g column, 20% ethyl acetate in heptane).

Sources & evidence

ORD record
ord-bb6834c2cc67450abf3c2210882c0813
Source dataset
uspto-grants-2005_11
Patent number
US06964965B2

Reaction notes

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