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

HRID 58220

Reaction equation

HRID 58220 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-12a77f0195e34611a0daedc0d4367fed
Source dataset
uspto-grants-2016_09
Patent number
US09434746B2

Linked notes

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