Benzenepropanoyl chloride → N-(4-oxo-3,4-dihydro-pyrimido[4,5-d]pyrimidin-2-ylmethyl)-3-phenyl-propionamide

HRID 2076837Notes

Reaction equation

HRID 2076837 reaction equation
[NH2:1][CH2:2][C:3]1[NH:4][C:5](=[O:13])[C:6]2[C:7]([N:12]=1)=[N:8][CH:9]=[N:10][CH:11]=2.CCN(C(C)C)C(C)C.[C:23]1([CH2:29][CH2:30][C:31](Cl)=[O:32])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C1COCC1>[O:13]=[C:5]1[C:6]2[C:7](=[N:8][CH:9]=[N:10][CH:11]=2)[N:12]=[C:3]([CH2:2][NH:1][C:31](=[O:32])[CH2:30][CH2:29][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[NH:4]1

Participants

5

Reactant 3

HCID 64801Benzenepropanoyl chlorideHCID 81531DiisopropylethylamineHCID 136366828HCID 136366828, compound

Product 1

HCID 136367003N-(4-oxo-3,4-dihydro-pyrimido[4,5-d]pyrimidin-2-ylmethyl)-3-phenyl-propionamideYield 3.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 2-aminomethyl-3H-pyrimido[4,5-d]pyrimidin-4-one (12 mg, 0.068 mmol) in THF (0.2 mL) and DIPEA (0.050 mL, 0.29 mmol) was added 3-phenyl-propionyl chloride (14 mg, 0.08 mmol) at ambient temperature. The reaction mixture was stirred one hour, evaporated and purified by column chromatography (silica gel, EtOAc/MeOH, 1/1) to yield N-(4-oxo-3,4-dihydro-pyrimido[4,5-d]pyrimidin-2-ylmethyl)-3-phenyl-propionamide as a white solid (0.8 mg, 3.8%). MS (m/e): 310.3 [M+H+].

Workup

  1. customevaporated
  2. custompurified by column chromatography (silica gel, EtOAc/MeOH, 1/1)

Sources & evidence

ORD record
ord-2999932d95764f84bf0699b7ff2fd3c4
Source dataset
uspto-grants-2011_04
Patent number
US07928106B2

Reaction notes

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