Cyclopentylamine → Cyclopentyl-(5-phenylethynyl-pyrimidin-2-yl)-amine

HRID 1942168Notes

Reaction equation

CS([C:5]1[N:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:7][N:6]=1)(=O)=O.[CH:19]1([NH2:24])[CH2:23][CH2:22][CH2:21][CH2:20]1.CCN(CC)CC>C1COCC1>[CH:19]1([NH:24][C:5]2[N:10]=[CH:9][C:8]([C:11]#[C:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:7][N:6]=2)[CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

Conditions

Temperature: 65 °C

Procedure

2-Methanesulfonyl-5-phenylethynyl-pyrimidine (100 mg, 3.11 mmol), cyclopentylamine (80 μl, 6.22 mmol) and Et3N (110 μl, 6.22 mmol) were suspended in 1 ml THF and stirred for 1 hour at 65° C. The reaction mixture was concentrated in vacuo and the residue was purified by flash chromatography by directly loading the crude material onto a silica gel column and eluting with (heptane:ethyl acetate 100:0→0:100). The desired compound was obtained as a white solid (85 mg, 83%), MS: m/e=264.2 (M+H+).

Workup

concentrationThe reaction mixture was concentrated in vacuo
customthe residue was purified by flash chromatography
washeluting with (heptane:ethyl acetate 100:0→0:100)

Sources & evidence

ORD record: ord-d7a1b950d9f84b308eab35c95a2c91c2
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08389536B2

Reaction notes

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