Methyl formate → HCID 11385587, compound

HRID 1243166Notes

Reaction equation

HRID 1243166 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:18][C:17]3[C:12](=[N:13][C:14]([NH:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[N:15][CH:16]=3)[N:11]([CH:26]3[CH2:31][CH2:30][CH2:29][NH:28][CH2:27]3)[C:10]2=[O:32])=[CH:5][CH:4]=1.[CH3:33][O:34]C=O>>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N:9]2[CH2:18][C:17]3[C:12](=[N:13][C:14]([NH:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[N:15][CH:16]=3)[N:11]([CH:26]3[CH2:31][CH2:30][CH2:29][N:28]([CH:33]=[O:34])[CH2:27]3)[C:10]2=[O:32])=[CH:7][CH:8]=1

Participants

3

Reactant 2

HCID 7865Methyl formateHCID 11235766HCID 11235766, compound

Product 1

HCID 11385587HCID 11385587, compound

Procedure

3-(4-Methoxy-phenyl)-7-phenylamino-1-piperidin-3-yl-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one (95 mg, 0.22 mmol) (from Example 4b supra) was dissolved at room temperature in methylformate (5 mL) (Aldrich). After stirring overnight the reaction mixture was concentrated to the crude product, which was purified by silica gel column chromatography with a 0–100% ethyl acetate in hexanes and then a 0–20% tetrahydrofuran in ethyl acetate gradient. After a precipitation out of dichloromethane with excess of pentane, 3-[3-(4-methoxy-phenyl)-2-oxo-7-phenylamino-3,4-dihydro-2H-pyrimido[4,5-d]pyrimidin-1-yl]-piperidine-1-carbaldehyde was isolated as an off-white solid. (Yield 90 mg, 89%).

Workup

  1. concentrationwas concentrated to the crude product, which
  2. customwas purified by silica gel column chromatography with a 0–100% ethyl acetate in hexanes
  3. customAfter a precipitation out of dichloromethane with excess of pentane

Sources & evidence

ORD record
ord-c0df0d85864f47c38dd7aae4a90f4c9e
Source dataset
uspto-grants-2006_10
Patent number
US07115740B2

Reaction notes

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