Tetrahydrofuran → (3-Amino-5,6-dichloropyrazin-2-yl)methanol

HRID 1981155Notes

Reaction equation

HRID 1981155 reaction equation
O1CCCC1.[NH2:6][C:7]1[C:12]([C:13](OC)=[O:14])=[N:11][C:10]([Cl:17])=[C:9]([Cl:18])[N:8]=1.[BH4-].[K+].[Cl-].[Li+]>O>[NH2:6][C:7]1[C:12]([CH2:13][OH:14])=[N:11][C:10]([Cl:17])=[C:9]([Cl:18])[N:8]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 73828Methyl 3-amino-5,6-dichloropyrazine-2-carboxylateHCID 433294Lithium ChlorideHCID 4192641Potassium borohydride

Product 1

HCID 13367870(3-Amino-5,6-dichloropyrazin-2-yl)methanol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 70 ml of dry tetrahydrofuran there was added 2-amino-5,6-dichloro-3-(methoxycarbonyl)pyrazine (8.8 g; 0.04 M), potassium borohydride (2.7 g; 0.05 M), and lithium chloride (2.1 g; 0.05 M), and the mixture was stirred at room temperature overnight (17 hours). The reaction mixture was then diluted with about 200 ml of water and chilled, after which the product crystallized, was filtered and dried (5.3 g).

Workup

  1. temperaturechilled
  2. customafter which the product crystallized
  3. filtrationwas filtered
  4. customdried (5.3 g)

Sources & evidence

ORD record
ord-6fe616fa27fd4f20a931c6955cc45eaf
Source dataset
uspto-grants-1985_04
Patent number
US04512991

Reaction notes

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