Sodium hydride → HCID 131736065, compound

HRID 1050349Notes

Reaction equation

[Cl:1][C:2]1[N:11]=[CH:10][C:9]2[C:8](=[O:12])[NH:7][CH:6]=[N:5][C:4]=2[CH:3]=1.[H-].[Na+].[CH3:15][Si:16]([CH3:23])([CH3:22])[CH2:17][CH2:18][O:19][CH2:20]Cl>CN(C)C=O>[Cl:1][C:2]1[N:11]=[CH:10][C:9]2[C:8](=[O:12])[N:7]([CH2:20][O:19][CH2:18][CH2:17][Si:16]([CH3:23])([CH3:22])[CH3:15])[CH:6]=[N:5][C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

In a dried round bottom flask under N2 atmosphere was added 7-chloro-3H-pyrido[4,3-d]pyrimidin-4-one (3, 9.0 g, 49.56 mmol) to dimethylformamide (50 mL). The solution was stirred at 0° C. and sodium hydride (1.78 g, 74.35 mmol) was added portion-wise over 10 min. The anionic suspension was stirred for 1 h at 0° C. followed by the addition of 2-(trimethylsilyl)ethoxymethyl chloride (12.4 g, 74.35 mmol) at 0° C. The reaction mixture was stirred at room temperature for 5 h. After consumption of starting materials as indicated by TLC, the reaction mixture was quenched with ice. A solid precipitates. It was filtered and washed with excess n-pentane. The solid was dried under vacuum to afford 7-chloro-3-(2-trimethylsilylethoxymethyl)pyrido[4,3-d]pyrimidin-4-one (4) as a brown solid. Yield: 9.1 g, 59%; 1H NMR (400 MHz, DMSO-d6) δ 9.17 (s, 1H), 8.72 (s, 1H), 7.79 (s, 1H), 5.49 (s, 2H), 3.65 (t, J=16 Hz, 2H), 0.90 (t, J=16 Hz, 2H), −0.03 (s, 9H).

Workup

stirringThe anionic suspension was stirred for 1 h at 0° C.
stirringThe reaction mixture was stirred at room temperature for 5 h
customAfter consumption of starting materials
customthe reaction mixture was quenched with ice
customA solid precipitates
filtrationIt was filtered
washwashed with excess n-pentane
customThe solid was dried under vacuum

Sources & evidence

ORD record: ord-b953bfa1c4ef4b84ba66fc96949b2fed
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09382248B2

Reaction notes

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