3-Pentanamine → HCID 11385264, compound

HRID 969295Notes

Reaction equation

C(O[C:4](=[O:26])[CH2:5][CH2:6][C:7]1[C:8](Cl)=[N:9][C:10]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([CH:21]([CH3:23])[CH3:22])=[CH:17][C:16]=2[Br:24])=[N:11][C:12]=1[CH3:13])C.[CH2:27]([CH:29]([NH2:32])[CH2:30][CH3:31])[CH3:28]>CN1CCCC1=O>[Br:24][C:16]1[CH:17]=[C:18]([CH:21]([CH3:23])[CH3:22])[CH:19]=[CH:20][C:15]=1[NH:14][C:10]1[N:11]=[C:12]([CH3:13])[C:7]2[CH2:6][CH2:5][C:4](=[O:26])[N:32]([CH:29]([CH2:30][CH3:31])[CH2:27][CH3:28])[C:8]=2[N:9]=1

Participants

Conditions

Temperature: 130 °C

Procedure

A solution of 3-[2-(2-bromo-4-isopropyl-phenylamino)-4-chloro-6-methyl-pyrimidin-5-yl]-propionic acid ethyl ester (XII; 0.22 g, 0.50 mmol) in N-methylpyrrolidinone (2.5 mL) was treated with 1-ethyl-propylamine (0.22 g, 2.5 mmol) and heated to 130° C. in a sealed tube for 130 hours. The cooled reaction mixture was poured onto water (50 mL) and extracted with diethyl ether (3×50 mL). The combined extracts were washed with brine (50 mL), dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The brown solid was chromatographed over silica gel, eluting with 20% ethyl acetate in hexane, to provide 113 as a white solid (0.11 g, 43%; mp 124-126° C.; ESIMS m/z (M+H) 445).

Workup

customThe cooled reaction mixture
additionwas poured onto water (50 mL)
extractionextracted with diethyl ether (3×50 mL)
washThe combined extracts were washed with brine (50 mL)
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe brown solid was chromatographed over silica gel
washeluting with 20% ethyl acetate in hexane

Sources & evidence

ORD record: ord-c6015c8bb33b48a6bebfd8916d8d808c
Source dataset: uspto-grants-2007_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07307082B2

Reaction notes

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