1-(Methylsulfanyl)propan-2-amine → 4-(2-chloro-4-pyridinyl)-N-[1-methyl-2-(methylthio)ethyl]-2-pyrimidinamine

HRID 913289Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([Cl:14])[CH:9]=2)[CH:5]=[CH:4][N:3]=1.[CH3:15][S:16][CH2:17][CH:18]([NH2:20])[CH3:19]>C1(C)C=CC=CC=1>[Cl:14][C:10]1[CH:9]=[C:8]([C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH:20][CH:18]([CH3:19])[CH2:17][S:16][CH3:15])[N:7]=2)[CH:13]=[CH:12][N:11]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 2-chloro-4-(2-chloro-4-pyridinyl)pyrimidine (i.e., the product of Example 6, Step A) (350 mg, 1.5 mmol) in toluene (4.0 mL) was added 1-(methylthio)-2-propanamine (i.e., the product of Step B) (1 mL, 9.5 mmol) in one portion; this mixture was heated at 60° C. for 18 h. The mixture was allowed to cool and silica gel (300 mg) was added. The excess solvent was removed under reduced pressure, and the resulting solid was chromatographed on silica gel eluted with a solvent gradient of 5% to 60% ethyl acetate in hexanes to give 400 mg (88%) of the title compound as a tan solid, m.p. 103-106° C.

Workup

temperatureto cool
additionsilica gel (300 mg) was added
customThe excess solvent was removed under reduced pressure
customthe resulting solid was chromatographed on silica gel
washeluted with a solvent gradient of 5% to 60% ethyl acetate in hexanes

Sources & evidence

ORD record: ord-9d74fb1551304cd48b20909b6be9434c
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08026359B2

Reaction notes

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