4-Chloro-2-(methylthio)pyrimidine-5-carboxylic acid ethyl ester → Ethyl 4-(methylamino)-2-(methylsulfanyl)pyrimidine-5-carboxylate

HRID 336516

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[C:7](Cl)=[N:8][C:9]([S:12][CH3:13])=[N:10][CH:11]=1)=[O:5])[CH3:2].C[CH2:16][N:17](C(C)C)C(C)C.Cl.CN>C(#N)C>[CH3:16][NH:17][C:7]1[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])=[CH:11][N:10]=[C:9]([S:12][CH3:13])[N:8]=1

Participants

Conditions

Temperature: 100 °C

Procedure

4-Chloro-2-methylsulfanyl-pyrimidine-5-carboxylic acid ethyl ester (10 g, 429 mmol) was dissolved in acetonitrile to which DIPEA (4.34 g, 642 mmol) and methylamine hydrochloride (11.10 g, 858 mmol) was added. The reaction mixture was stirred at 100° C. for 3 hours, then cooled to room temperature and poured in to ice water. Off-white crystalline solid precipitated out. The solid was collected by filtration on a Buchner funnel and dried under vacuum to give the desired product (11 g). 1H NMR (DMSO-d6): δ 1.30 (t, J=7 Hz, 3H), δ 2.46 (s, 3H), δ 2.99 (d, J=5 Hz, 3H), δ 4.29 (q, J=7 Hz, 2H), δ 8.09 (br, s, 1H), δ 8.53 (s, 1H).

Workup

additionwas added
temperaturecooled to room temperature
customOff-white crystalline solid precipitated out
filtrationThe solid was collected by filtration on a Buchner funnel
customdried under vacuum

Sources & evidence

ORD record: ord-a4b193244f334bc8b176808aa1d83f85
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08889696B2

Linked notes

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