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Ammonia → 2-(5-Amino-2-methylphenylamino)-2-(thieno[2,3-b]pyrazin-6-yl)acetonitrile

HRID 1184888
Notes
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Reaction equation

HRID 1184888 reaction equation
S(S([O-])=O)([O-])=O.[Na+].[Na+].N.[CH3:10][C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][C:12]=1/[N:20]=[C:21](\[C:31]#[N:32])/[C:22]1[S:30][C:25]2=[N:26][CH:27]=[CH:28][N:29]=[C:24]2[CH:23]=1>O.O1CCOCC1>[NH2:17][C:14]1[CH:15]=[CH:16][C:11]([CH3:10])=[C:12]([NH:20][CH:21]([C:22]2[S:30][C:25]3=[N:26][CH:27]=[CH:28][N:29]=[C:24]3[CH:23]=2)[C:31]#[N:32])[CH:13]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 222AmmoniaHCID 24489Sodium DithioniteHCID 178426707HCID 178426707, compound

Product 1

HCID 671255562-(5-Amino-2-methylphenylamino)-2-(thieno[2,3-b]pyrazin-6-yl)acetonitrileYield 85%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent
HCID 31275
1,4-Dioxane
Solvent

Procedure

To a solution of sodium hydrosulfite (434 mg, 2.493 mmol) in water (3 mL) was added ammonia (0.561 mL, 3.64 mmol) and then compound 77 (62 mg, 0.192 mmol) in dioxane (3 mL). The reaction was stirred at rt. for 4 h. Quenched with water and extracted with EtOAc. Organic layer was washed with brine, dried and evaporated to give compound 2-(5-amino-2-methylphenylamino)-2-(thieno[2,3-b]pyrazin-6-yl)acetonitrile 78 (48 mg, 85%) which was used without further purification. (m/z)=296 (M+H)+.

Workup

  1. customQuenched with water
  2. extractionextracted with EtOAc
  3. washOrganic layer was washed with brine
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-2a9a357a860141fca2c597b9db318ef7
Source dataset
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08669256B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes