Phosphorus sulfide (P2S5) → 2-Aminopyridine-3-carbothioamide

HRID 1927247Notes

Reaction equation

HRID 1927247 reaction equation
[NH2:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=O.C[Si](C)(C)O[Si](C)(C)C.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:21]>CN(C)P(N(C)C)(N(C)C)=O>[NH2:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[S:21]

Participants

5

Reactant 3

HCID 14817Phosphorus sulfide (P2S5)HCID 24764HexamethyldisiloxaneHCID 5066232-Aminopyridine-3-carboxamide

Product 1

HCID 226330932-Aminopyridine-3-carbothioamideYield 88.6%

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Conditions

Temperature
110 °C

Procedure

2-Amino-nicotinamide (1.6 g) described in Manufacturing Example 14-1, hexamethyldisiloxane (3.2 g), phosphorus pentasulfide (950 mg), and hexamethylphosphoramide (13 mL) were stirred for 18 hours at 110° C. The reaction solution was passed through a glass filter (eluted with ethyl acetate) lined with NH-silica gel and silica gel in a 1:1 ratio. The eluate was purified by NH silica gel column chromatography (heptane:ethyl acetate=1:1) to obtain the titled compound (290 mg).

Workup

  1. filtrationfilter
  2. wash(eluted with ethyl acetate)
  3. customThe eluate was purified by NH silica gel column chromatography (heptane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-d92eda7c587247908263f924998f1cb9
Source dataset
uspto-grants-2012_05
Patent number
US08183264B2

Reaction notes

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