Ethanol → 5-[3-Methyl-5-(morpholine-4-carbonyl)-1H-pyrrol-2-ylmethylene]-4-piperidin-1-YL-5,7-dihydro-pyrrolo[2,3-D]pyrimidin-6-one

HRID 397428Notes

Reaction equation

HRID 397428 reaction equation
Cl[C:2]1[C:3]2[CH2:10][C:9](=[O:11])[NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[CH3:12][C:13]1[CH:17]=[C:16]([C:18]([N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)=[O:19])[NH:15][C:14]=1[CH:26]=O.[CH2:28](O)[CH3:29]>N1CCCCC1>[CH3:12][C:13]1[CH:17]=[C:16]([C:18]([N:20]2[CH2:21][CH2:22][O:23][CH2:24][CH2:25]2)=[O:19])[NH:15][C:14]=1[CH:26]=[C:10]1[C:3]2[C:2]([N:5]3[CH2:29][CH2:28][CH2:2][CH2:3][CH2:4]3)=[N:7][CH:6]=[N:5][C:4]=2[NH:8][C:9]1=[O:11]

Participants

5

Reactant 3

HCID 702EthanolHCID 120958704-chloro-5H,6H,7H-pyrrolo[2,3-d]pyrimidin-6-oneHCID 223910003-methyl-5-(morpholine-4-carbonyl)-1H-pyrrole-2-carbaldehyde

Product 1

HCID 498233385-[3-Methyl-5-(morpholine-4-carbonyl)-1H-pyrrol-2-ylmethylene]-4-piperidin-1-YL-5,7-dihydro-pyrrolo[2,3-D]pyrimidin-6-oneYield 79%

Reagents, catalysts & solvents 1

HCID 8082PiperidineCatalyst

Procedure

A mixture of 4-chloro-5,7-dihydro-pyrrolo[2,3-d]pyrimidin-6-one (169 mg, 1 mmol), 3-methyl-5-(morpholine-4-carbonyl)-1H-pyrrole-2-carbaldehyde (222 mg, 1 mmol) and piperidine (2 drops) in ethanol (3 mL) was heated to reflux for overnight. The precipitate was collected by vacuum filtration, washed with ethyl acetate/hexane and dried to give 332.2 mg (79%) of the title compound as a yellow solid. MS 423 [M++1].

Workup

  1. temperaturewas heated
  2. temperatureto reflux for overnight
  3. filtrationThe precipitate was collected by vacuum filtration
  4. washwashed with ethyl acetate/hexane
  5. customdried

Sources & evidence

ORD record
ord-2d03ea3d18d740c2ba7a94e8818df5ba
Source dataset
uspto-grants-2003_08
Patent number
US06610688B2

Reaction notes

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