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Ammonia → (2-Aminopyrimidin-4-yl)(1,3-benzothiazol-2-yl)acetonitrile

HRID 854265
Notes
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Reaction equation

HRID 854265 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH:10]([C:13]1[CH:18]=[CH:17][N:16]=[C:15](Cl)[N:14]=1)[C:11]#[N:12].[NH3:20]>C(O)C>[NH2:20][C:15]1[N:14]=[C:13]([CH:10]([C:2]2[S:1][C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[N:3]=2)[C:11]#[N:12])[CH:18]=[CH:17][N:16]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 222AmmoniaHCID 3952292-(Benzo[d]thiazol-2-yl)-2-(2-chloropyrimidin-4-yl)acetonitrile

Product 1

HCID 17906827(2-Aminopyrimidin-4-yl)(1,3-benzothiazol-2-yl)acetonitrileYield 51%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
150 °C

Procedure

A suspension of 1 (0.1 g, 0.35 mmol) in a 2M solution of ammonia in ethanol (10 ml) was heated up to 150° C. in a Parr vessel for 3 h. The solution was cooled down to r.t. and the yellow precipitate formed was filtered off then washed thoroughly with ethanol/water 1:1 and water. The precipitate was dried in vacuum at 40° C. affording 48 mg (51%) of the title compound as a yellow powder.

Workup

  1. temperatureThe solution was cooled down to r.t.
  2. customthe yellow precipitate formed
  3. filtrationwas filtered off
  4. washthen washed thoroughly with ethanol/water 1:1 and water
  5. customThe precipitate was dried in vacuum at 40° C.

Sources & evidence

ORD record
ord-e9dc4f0f2a5e462ea4308e39e7e503af
Source dataset
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07259162B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes