Potassium Carbonate → (R)-2-(2,5-dichloro-pyrimidin-4-ylamino)-3-methyl-butyramide

HRID 1041733

반응식

HRID 1041733 반응식
[NH2:1][C@H:2]([CH:6]([CH3:8])[CH3:7])[C:3]([NH2:5])=[O:4].[Cl:9][C:10]1[N:15]=[C:14](Cl)[C:13]([Cl:17])=[CH:12][N:11]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.C(Cl)Cl>[Cl:9][C:10]1[N:15]=[C:14]([NH:1][C@H:2]([CH:6]([CH3:8])[CH3:7])[C:3]([NH2:5])=[O:4])[C:13]([Cl:17])=[CH:12][N:11]=1

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 2372592,4,5-TrichloropyrimidineHCID 444079(R)-2-amino-3-methylbutanamide

생성물 1

HCID 86634077(R)-2-(2,5-dichloro-pyrimidin-4-ylamino)-3-methyl-butyramide수율 62.4%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

A mixture of (R)-2-amino-3-methyl-butyramide (50 mg), 2,4,5-trichloropyrimidine (67 mg) and K2CO3 (116 mg) in DMF (3 mL) was stirred at room temperature for 5 hr. The reaction mixture was diluted with DCM and washed with brine three times. The organic layer was dried with sodium sulfate and concentrated. The residue was purified by silica gel chromatography to provide 60 mg of (R)-2-(2,5-dichloro-pyrimidin-4-ylamino)-3-methyl-butyramide: 1H NMR (300 MHz, CDCl3) 8.2 (s, 1H), 6.2 (bs, 1H), 5.8 (bs, 1H), 5.6 (bs, 1H), 4.6 (dd, 1H), 2.4 (m, 1H), 1.2 (d, 6H). MS (m/e) 263 (M+1).

후처리

  1. washwashed with brine three times
  2. dry with materialThe organic layer was dried with sodium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-ca9b4177ec1d419692fd65d148724ee5
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08552186B2

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