Diisopropylethylamine → (S)-7-chloro-5-(3-(hydroxymethyl)pyrrolidin-1-yl)-3-methylpyrido[4,3-d]pyrimidin-4(3H)-one

HRID 1023305Notes

Reaction equation

Cl[C:2]1[C:11]2[C:10](=[O:12])[N:9]([CH3:13])[CH:8]=[N:7][C:6]=2[CH:5]=[C:4]([Cl:14])[N:3]=1.[NH:15]1[CH2:19][CH2:18][C@H:17]([CH2:20][OH:21])[CH2:16]1.CCN(C(C)C)C(C)C>O1CCOCC1>[Cl:14][C:4]1[N:3]=[C:2]([N:15]2[CH2:19][CH2:18][C@H:17]([CH2:20][OH:21])[CH2:16]2)[C:11]2[C:10](=[O:12])[N:9]([CH3:13])[CH:8]=[N:7][C:6]=2[CH:5]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 5,7-dichloro-3-methylpyrido[4,3-d]pyrimidin-4(3H)-one (270 mg, 1.17 mmol), (S)-pyrrolidin-3-ylmethanol (1.40 mmol), Hunig's base (1.02 mL, 5.85 mmol) and dioxane (4 mL) was stirred at 100° C. overnight. The reaction mixture was cooled to room temperature and worked-up. The residue was purified using slilica gel flash column chromatography (eluent: 0-10% methanol in dichloromethane) to afford (S)-7-chloro-5-(3-(hydroxymethyl)pyrrolidin-1-yl)-3-methylpyrido[4,3-d]pyrimidin-4(3H)-one as a white solid.

Workup

temperatureThe reaction mixture was cooled to room temperature
customThe residue was purified

Sources & evidence

ORD record: ord-15f8ef4b80ee4f26b4b0b50b67ad513b
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722692B2

Reaction notes

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