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Dimethylformamide → 5-(Dimethylphosphoryl)-3-methoxypyrazin-2-amine

HRID 921328
Notes
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Reaction equation

HRID 921328 reaction equation
Br[C:2]1[CH:7]=[N:6][CH2:5][C:4](N)([O:8][CH3:9])[N:3]=1.[CH3:11][PH:12](=[O:14])[CH3:13].P([O-])([O-])([O-])=O.[K+].[K+].[K+].C[N:24](C=O)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>[CH3:11][P:12]([C:2]1[N:3]=[C:4]([O:8][CH3:9])[C:5]([NH2:24])=[N:6][CH:7]=1)([CH3:13])=[O:14]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 62657Potassium Phosphate, TribasicHCID 670526695-Bromo-3-methoxypyrazin-3-ylamineHCID 178503022methylphosphonoylmethane

Product 1

HCID 670526825-(Dimethylphosphoryl)-3-methoxypyrazin-2-amineYield 63%

Reagents, catalysts & solvents 2

HCID 167845
palladium(II) acetate
Catalyst
HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)Catalyst

Procedure

To a solution of 5-bromo-3-methoxypyrazin-3-ylamine (0.204 g, 1.00 mmol) in 4 mL DMF was added dimethylphosphine oxide (0.171 g, 1.10 mmol), palladium acetate (11.0 mg, 0.0490 mmol), XANTPHOS (35.0 mg, 0.0600 mmol), and potassium phosphate (0.233 g, 1.10 mmol). The mixture was purged with nitrogen, and subjected to microwaves at 150° C. for 20 minutes. The reaction mixture was concentrated and purified by silica gel chromatography (0-10% 7N ammonia in methanol:dichloromethane) to afford the desired product (126 mg, 63% yield).

Workup

  1. customThe mixture was purged with nitrogen
  2. concentrationThe reaction mixture was concentrated
  3. custompurified by silica gel chromatography (0-10% 7N ammonia in methanol:dichloromethane)

Sources & evidence

ORD record
ord-29c7c4a2c65e4b50943190731e0fd74f
Source dataset
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09273077B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes