Pivaloyl chloride → 2,2-Dimethyl-N-(7-methyl-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-2-yl)propanamide

HRID 598183Notes

Reaction equation

[NH2:1][C:2]1[NH:3][C:4](=[O:12])[C:5]2[CH:10]=[CH:9][N:8]([CH3:11])[C:6]=2[N:7]=1.[C:13](Cl)(=[O:18])[C:14]([CH3:17])([CH3:16])[CH3:15]>N1C=CC=CC=1.O>[CH3:15][C:14]([CH3:17])([CH3:16])[C:13]([NH:1][C:2]1[NH:3][C:4](=[O:12])[C:5]2[CH:10]=[CH:9][N:8]([CH3:11])[C:6]=2[N:7]=1)=[O:18]

Participants

Conditions

Temperature: 80 °C

Procedure

To a suspension of 2-amino-7-methyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one (4.82 g, 29.4 mmol) in pyridine (45 ml) was added pivaloyl chloride (11.6 ml, 94.0 mmol) at 0° C., and the mixture was stirred at 80° C. for 2 hours. After cooling, the reaction mixture was diluted with water and extracted with ethyl acetate (×1). The organic layer was washed with water (×1) and brine (×1), dried over sodium sulfate and concentrated in vacuo. The residual solids were suspended in methanol (45 ml), and concentrated aqueous ammonia (10 ml) was added at 0° C. The suspension was stirred at the same temperature for 30 minutes, before addition of water. After stirring at 0° C. for 2 hours, the resulting crystals were collected by filtration and washed with water to give 5.46 g (75%) of the title compound.

Workup

temperatureAfter cooling
extractionextracted with ethyl acetate (×1)
washThe organic layer was washed with water (×1) and brine (×1)
dry with materialdried over sodium sulfate
concentrationconcentrated in vacuo
additionconcentrated aqueous ammonia (10 ml) was added at 0° C
stirringThe suspension was stirred at the same temperature for 30 minutes, before addition of water
stirringAfter stirring at 0° C. for 2 hours
filtrationthe resulting crystals were collected by filtration
washwashed with water

Sources & evidence

ORD record: ord-157df0ff513648639f9e942405267900
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07897607B2

Reaction notes

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