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

HRID 921446
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HRID 921446 반응식
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]
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참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

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

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-9fea3ebca5c84fe4b727d191c0b68c2e
출처 데이터셋
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09273077B2

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