Adenine → 2-[1-(6-amino-9H-purin-9-yl)ethyl]-3-bromo-6-methyl-4H-pyrido[1,2-a]pyrimidin-4-one

HRID 58220

반응식

HRID 58220 반응식
[Br:1][C:2]1[C:7](=[O:8])[N:6]2[C:9]([CH3:13])=[CH:10][CH:11]=[CH:12][C:5]2=[N:4][C:3]=1[CH:14](Cl)[CH3:15].[N:17]1[C:25]([NH2:26])=[C:24]2[C:20]([N:21]=[CH:22][NH:23]2)=[N:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[NH2:26][C:25]1[N:17]=[CH:18][N:19]=[C:20]2[C:24]=1[N:23]=[CH:22][N:21]2[CH:14]([C:3]1[N:4]=[C:5]2[CH:12]=[CH:11][CH:10]=[C:9]([CH3:13])[N:6]2[C:7](=[O:8])[C:2]=1[Br:1])[CH3:15]

참가 물질

6

반응물 4

HCID 190AdenineHCID 962WaterHCID 11430Potassium CarbonateHCID 668640303-bromo-2-(1-chloroethyl)-6-methyl-4H-pyrido[1,2-a]pyrimidin-4-one

생성물 1

HCID 668647722-[1-(6-amino-9H-purin-9-yl)ethyl]-3-bromo-6-methyl-4H-pyrido[1,2-a]pyrimidin-4-one수율 10.7%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A mixture of 3-bromo-2-(1-chloroethyl)-6-methyl-4H-pyrido[1,2-a]pyrimidin-4-one (1.24 g, 4.11 mmol), adenine (Sigma, 1.08 g, 8.04 mmol), and potassium carbonate (1.11 g, 8.04 mmol) in N,N-dimethylformamide (20 mL) was stirred at room temperature overnight. The suspension was then poured into water and extracted with methylene chloride. The combined organic layers were washed with water, brine, and then the organic layers dried and evaporated to dryness. The residue was chromatographed on silica gel, eluting with 0 to 10% MeOH in methylene chloride, to provide the desired product (176 mg, 10.7%). LCMS calculated for C16H15BrN7O (M+H)+: m/z=400.1. Found: 400.1. 1H NMR (DMSO-d6, 300 MHz) δ 8.44 (1H, s), 8.07 (1H, s), 7.67 (1H, dd, J=8.7 and 7.2 Hz), 7.30 (1H, br d, J=8.7 Hz), 7.20 (2H, s), 6.99 (1H, br d, J=7.2 Hz), 6.15 (1H, q, J=7.2 Hz), 2.91 (3H, s), 1.84 (3H, d, J=7.2 Hz) ppm.

후처리

  1. extractionextracted with methylene chloride
  2. washThe combined organic layers were washed with water, brine
  3. customthe organic layers dried
  4. customevaporated to dryness
  5. customThe residue was chromatographed on silica gel
  6. washeluting with 0 to 10% MeOH in methylene chloride

출처 및 근거

ORD 기록
ord-12a77f0195e34611a0daedc0d4367fed
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434746B2

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