3-Phenylpropylamine → HCID 12096129, compound

HRID 480421Notes

Reaction equation

C[Si](C)(C)[C:3]#[C:4][CH2:5][N:6]1[C:11](=[O:12])[C:10]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)=[C:9]([C:20]2[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=2)[N:8]=[C:7]1SC.[C:30]1([CH2:36][CH2:37][CH2:38][NH2:39])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>>[F:19][C:16]1[CH:17]=[CH:18][C:13]([C:10]2[C:11](=[O:12])[N:6]3[CH:5]=[C:4]([CH3:3])[N:39]([CH2:38][CH2:37][CH2:36][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[C:7]3=[N:8][C:9]=2[C:20]2[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=2)=[CH:14][CH:15]=1

Participants

Reactant 2

HCID 162593-Phenylpropylamine

HCID 12096128HCID 12096128, compound

Product 1

HCID 12096129HCID 12096129, compound

Conditions

Temperature: 190 °C

Procedure

A neat mixture of 3-(3-trimethylsilyl-2-propynyl)-5-(4-fluorophenyl)-2-methylthio-6-(4-pyridyl)-4(3H)-pyrimidinone (50 mg, 0.12 mmol) and 3-phenyl-1-propylamine (67 mg, 0.47 mmol) was warmed to 190° C. for 17 h. After cooling to 23° C., the reaction mixture was applied directly to purification via flash chromatography (step gradient 1%MeOH:CHCl3 then 2%, then 3%;) to afford the desired product: MS (m/z) 439 (M+H)+.

Workup

temperatureAfter cooling to 23° C.
customthe reaction mixture was applied directly to purification via flash chromatography (step gradient 1%MeOH

Sources & evidence

ORD record: ord-8f0ef476e8cc4aaa9c99ff84895ab568
Source dataset: uspto-grants-2003_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06649604B2

Reaction notes

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