Hydrochloric Acid → HCID 87799380, compound

HRID 1280559Notes

Reaction equation

[NH:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8]2[N:13]=[C:12]3[N:14]([CH3:26])[C:15](=[O:25])[N:16]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=4[CH3:24])[CH2:17][C:11]3=[CH:10][N:9]=2)[CH2:3][CH2:2]1.[C:27]([O:31]C)(=O)[CH:28]=[CH2:29].C(N(CC)CC)C.Cl.C[CH2:42][O:43]CC>C(OCC)(=O)C.O1CCCC1.CN1CCCC1=O>[CH3:42][O:43][C:27](=[C:28]=[O:29])[CH2:31][N:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8]2[N:13]=[C:12]3[N:14]([CH3:26])[C:15](=[O:25])[N:16]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=4[CH3:24])[CH2:17][C:11]3=[CH:10][N:9]=2)[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 75 °C

Procedure

A mixture of 7-(piperidin-4-ylamino)-1-methyl-3-ortho-tolyl-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one (0.19 g, 0.54 mmol) (prepared as described in Example 25), 1.0 mL of methyl acrylate, 0.5 mL of triethylamine, 0.5 mL of 1-methyl-2-pyrrolidinone, and 5 mL of tetrahydrofuran was heated at 75° C. for 17 hours. The reaction mixture was evaporated under reduced pressure, and the residue was purified by chromatography on silica gel using 5% methanol in dichloromethane as eluant to give 132 mg (56%yield) of the product. 1M Hydrochloric acid in ether was added to a solution of the product in ethyl acetate, and the suspension stirred at room temperature for 1 hour. The mixture was evaporated under reduced pressure to give the hydrochloride salt of 7-[l-(2-methoxy-carbonylethyl)piperidin-4-ylamino]-1-methyl-3-ortho-tolyl-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one.

Workup

customThe reaction mixture was evaporated under reduced pressure
customthe residue was purified by chromatography on silica gel using 5% methanol in dichloromethane as eluant
customto give 132 mg (56%yield) of the product
customThe mixture was evaporated under reduced pressure

Sources & evidence

ORD record: ord-ba857f5dea1b45f0ade66db927488fbd
Source dataset: uspto-grants-2002_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06451804B1

Reaction notes

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