Tetrahydrofuran → (R)-6-amino-4-((1-methoxypropan-2-yl)oxy)nicotinonitrile

HRID 1777979Notes

Reaction equation

HRID 1777979 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[K+].[CH3:11][O:12][C@@H:13](O)[CH2:14][CH3:15].[NH2:17][C:18]1[CH:25]=[C:24](F)[C:21]([C:22]#[N:23])=[CH:20][N:19]=1.C1C[O:30]CC1>>[NH2:17][C:18]1[CH:25]=[C:24]([O:30][C@H:14]([CH3:15])[CH2:13][O:12][CH3:11])[C:21]([C:22]#[N:23])=[CH:20][N:19]=1

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran3×HCID 3251421Potassium bis(trimethylsilyl)amideHCID 92954563(R)-1-methoxypropanolHCID 1180369016-Amino-4-fluoronicotinonitrile2×

Product 1

HCID 118036909(R)-6-amino-4-((1-methoxypropan-2-yl)oxy)nicotinonitrile

Procedure

A solution of KHMDS in THF (1M, 43.8 ml, 43.8 mmol) was added to a solution of (R)-1-methoxypropanol (4.3 ml, 43.8 mmol) in THF (50 ml) at room temperature under a positive argon pressure. After stirring for 15 minutes at room temperature a solution of 6-amino-4-fluoronicotinonitrile (intermediate 21, 3.0 g, 21.88 mmol) in THF (30 ml) was added drop wise. The reaction mixture was stirred for 65 h at room temperature, partitioned between aqueous NH4Cl and

Workup

  1. additionwas added drop wise
  2. custompartitioned between aqueous NH4Cl

Sources & evidence

ORD record
ord-7e50e10a9f4344a48b699d88cf1a9547
Source dataset
uspto-grants-2016_02
Patent number
US09266883B2

Reaction notes

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