Tert-Butylamine → HCID 59540884, compound

HRID 1677364Notes

Reaction equation

HRID 1677364 reaction equation
[CH3:1][C:2]1[N:22]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])[C:5]2=[N:6][CH:7]=[C:8]([C:10]3[CH:15]=[C:14]([O:16][CH3:17])[C:13]([O:18][CH3:19])=[C:12]([O:20][CH3:21])[CH:11]=3)[N:9]=[C:4]2[C:3]=1[C:31]([OH:33])=O.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.[C:67]([NH2:71])([CH3:70])([CH3:69])[CH3:68]>CN(C=O)C>[C:67]([NH:71][C:31]([C:3]1[C:4]2[C:5](=[N:6][CH:7]=[C:8]([C:10]3[CH:15]=[C:14]([O:16][CH3:17])[C:13]([O:18][CH3:19])=[C:12]([O:20][CH3:21])[CH:11]=3)[N:9]=2)[N:22]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:28])([CH3:30])[CH3:29])[C:2]=1[CH3:1])=[O:33])([CH3:70])([CH3:69])[CH3:68]

Participants

5

Reactant 3

HCID 6385Tert-ButylamineHCID 2724699PyBOPHCID 59540829HCID 59540829, compound

Product 1

HCID 59540884HCID 59540884, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-Methyl-2-(3,4,5-trimethoxy-phenyl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (95 mg) in 1.5 mL of DMF was added PyBOP (128 mg) followed by tert-Butyl amine (70 mg). After stirring for 2 h, the mixture was partitioned between water and diethylether. The organic phase was washed with brine, dried over Na2SO4, filtered, and concentrated. Flash chromatography (4:1 Hexanes:ethylacetate) afforded 70 mg of 6-Methyl-2-(3,4,5-trimethoxy-phenyl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid tert-butylamide.

Workup

  1. customthe mixture was partitioned between water and diethylether
  2. washThe organic phase was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3d97b0acd20d4adf9ec03b0c37e67833
Source dataset
uspto-grants-2011_08
Patent number
US08008298B2

Reaction notes

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