Cyclopentylamine → 4-(Cyclopentylamino)-2-(methylthio)pyrimidine-5-carbaldehyde

HRID 1930400Notes

Reaction equation

HRID 1930400 reaction equation
Cl[C:2]1[C:7]([C:8]([O:10]CC)=O)=[CH:6][N:5]=[C:4]([S:13][CH3:14])[N:3]=1.[CH:15]1([NH2:20])[CH2:19][CH2:18][CH2:17][CH2:16]1>>[CH:15]1([NH:20][C:2]2[C:7]([CH:8]=[O:10])=[CH:6][N:5]=[C:4]([S:13][CH3:14])[N:3]=2)[CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

3

Reactant 2

HCID 2906CyclopentylamineHCID 800084-Chloro-2-(methylthio)pyrimidine-5-carboxylic acid ethyl ester

Product 1

HCID 107998964-(Cyclopentylamino)-2-(methylthio)pyrimidine-5-carbaldehydeYield 49.1%

Procedure

Ethyl 4-chloro-2-(methylthio)pyrimidine-5-carboxylate (17 g, 73 mmol) and cyclopentylamine (12.4 g, 146 mmol) were combined by the 3-step procedure of Example C1 to provide 4-cyclopentylamino-2-methylsulfanyl-pyrimidine-5-carbaldehyde (8.5 g, 49% yield over 3 steps). 1H NMR (400 MHz, DMSO-d6): δ 9.73 (s, 1 H), 8.55 (d, J=6.4 Hz, 1 H), 8.51 (s, 1 H), 4.43 (m, 1 H), 2.50 (s, 3 H, obscured by DMSO), 2.03-1.98 (m, 2 H), 1.69-1.48 (m, 6 H); MS (ESI) m/z: 238.3 [M+H]+.

Sources & evidence

ORD record
ord-f981015fbce44c13944cc8d95ec113b8
Source dataset
uspto-grants-2012_05
Patent number
US08188113B2

Reaction notes

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