Methanol → 1-(2-Isopropylamino-6-methyl-pyrimidin-4-yl)-ethanone oxime

HRID 2069469Notes

Reaction equation

Cl.[NH2:2][OH:3].[CH:4]([NH:7][C:8]1[N:13]=[C:12]([C:14](=O)[CH3:15])[CH:11]=[C:10]([CH3:17])[N:9]=1)([CH3:6])[CH3:5].CO>O.[OH-].[Na+]>[CH:4]([NH:7][C:8]1[N:13]=[C:12]([C:14](=[N:2][OH:3])[CH3:15])[CH:11]=[C:10]([CH3:17])[N:9]=1)([CH3:6])[CH3:5]

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of hydroxylamine hydrochloride (737 mg, 10.6 mmol) in water (3.0 mL) and 1 N aq. NaOH (11 mL) is added to 1-(2-isopropylamino-6-methyl-pyrimidin-4-yl)-ethanone (1.71 g, 8.85 mmol). The solution is stirred at 80° C. for 2 h and MeOH is added to maintain homogeneity of the mixture. The mixture is cooled to rt and the precipitate that forms is collected, washed with water and dried in vacuo to give 1-(2-isopropylamino-6-methyl-pyrimidin-4-yl)-ethanone oxime (1.54 g) as a yellow solid; LC-MS: tR=0.72 min, [M+H]+=209.52; 1H NMR (D6-DMSO): δ 1.15 (d, J=6.5 Hz, 6H), 2.10 (s, 3H), 2.25 (s, 3H), 4.07 (m, 1H), 6.80 (s, 1H), 6.86 (d, J=7.5 Hz, 1H), 11.62 (s, 1H).

Workup

temperatureto maintain homogeneity of the mixture
temperatureThe mixture is cooled to rt
customthe precipitate that forms is collected
washwashed with water
customdried in vacuo

Sources & evidence

ORD record: ord-5c6b09d1722447c68c9eef1b3a1a2883
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08299086B2

Reaction notes

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