tert-Butanol → tert-Butyl (5-methylpyrazin-2-yl)carbamate

HRID 1830718Notes

Reaction equation

HRID 1830718 reaction equation
C[C:2]1[N:3]=[CH:4][C:5]([C:8](O)=O)=[N:6][CH:7]=1.C([N:13]([CH2:16]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:25])C=CC=CC=1.[CH3:35][C:36]([OH:39])([CH3:38])[CH3:37]>C1(C)C=CC=CC=1.CCOC(C)=O>[C:36]([O:39][C:16](=[O:25])[NH:13][C:2]1[CH:7]=[N:6][C:5]([CH3:8])=[CH:4][N:3]=1)([CH3:38])([CH3:37])[CH3:35]

Participants

7

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 1228315-Methyl-2-pyrazinecarboxylic acidHCID 199401P,P-Diphenylphosphinic azide

Product 1

HCID 22046506tert-Butyl (5-methylpyrazin-2-yl)carbamate

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 5-methyl pyrazine carboxylic acid (13.8 g, 100 mmol) in 300 mL of toluene at room temperature under nitrogen was added triethyl amine (14 mL, 100 mmol) followed by diphenyl phosphoryl azide (21.6 mL, 100 mmol). After 30 min. at room temperature, 2-methyl-2-propanol (19 mL, 200 mmol) was added and the solution immersed in a 90 ° C. oil bath. After 2 hours, the reaction was cooled to RT, diluted to 600 mL with EtOAc, and washed 3×60 mL with 10% Na2CO3 and 1×600 mL with saturated NaCl. The organics were dried (MgSO4), filtered and concentrated to a yellow solid (17.5 g, 83%). 1H-NMR (400 MHz, CDCl3) δ9.16 (s, 1H), 8.05 (s, 1H), 7.56 (br s, 1H), 2.50 (s, 3H), 1.55 (s, 9H)

Workup

  1. customimmersed in a 90 ° C.
  2. waitAfter 2 hours
  3. washwashed 3×60 mL with 10% Na2CO3 and 1×600 mL with saturated NaCl
  4. dry with materialThe organics were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated to a yellow solid (17.5 g, 83%)

Sources & evidence

ORD record
ord-a318ec009a6d4e1a9ce34e73b67955b0
Source dataset
uspto-grants-2006_06
Patent number
US07067506B2

Reaction notes

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