Water → HCID 22477355, compound

HRID 549007Notes

Reaction equation

HRID 549007 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[C:3]2[NH:7][C:8]([C:10]3[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=3)[CH:13]=[O:14])=[CH:9][C:2]=12.[BH4-].[Na+].O>C(O)C>[N:1]1[CH:6]=[CH:5][N:4]=[C:3]2[NH:7][C:8]([C:10]3[CH:11]=[C:12]([CH2:13][OH:14])[CH:15]=[CH:16][CH:17]=3)=[CH:9][C:2]=12

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 9920895HCID 9920895, compound

Product 1

HCID 22477355HCID 22477355, compoundYield 86.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)-benzaldehyde [0.4 g, Example 9(a)] in ethanol (50 mL) was treated with sodium borohydride (200 mg). The mixture was allowed to stir at ambient temperature for 1 hour then treated with water (10 mL) and then evaporated. The residual solid was triturated with water (50 mL) to give a pale yellow solid which was washed with water and then recrystallised from methanol to yield the title compound (0.35 g) as a yellow crystalline solid, m.p. 225-226° C. [Elemental analysis:— C, 68.72; H, 4.73; N, 18.44%. Calculated for C13H11N3O:— C, 69.32; H, 4.92; N, 18.65%].

Workup

  1. customevaporated
  2. customThe residual solid was triturated with water (50 mL)
  3. customto give a pale yellow solid which
  4. washwas washed with water
  5. customrecrystallised from methanol

Sources & evidence

ORD record
ord-fbb8ab03e43344b0a1d12ae7c572dd43
Source dataset
uspto-grants-2011_05
Patent number
US07943616B2

Reaction notes

Loading…