Triethylamine → 2-[5-(4-Fluorophenyl)-4-[4-(methoxymethyl)-1-piperidyl]thieno[2,3-d]pyrimidin-2-yl]ethanol

HRID 928615Notes

Reaction equation

Cl[C:2]1[C:3]2[C:13]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)=[CH:12][S:11][C:4]=2[N:5]=[C:6]([CH2:8][CH2:9][OH:10])[N:7]=1.C(N(CC)CC)C.Cl.[CH3:29][O:30][CH2:31][CH:32]1[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1>C(O)C>[F:20][C:17]1[CH:18]=[CH:19][C:14]([C:13]2[C:3]3[C:2]([N:35]4[CH2:36][CH2:37][CH:32]([CH2:31][O:30][CH3:29])[CH2:33][CH2:34]4)=[N:7][C:6]([CH2:8][CH2:9][OH:10])=[N:5][C:4]=3[S:11][CH:12]=2)=[CH:15][CH:16]=1

Participants

Conditions

Temperature: 55 °C

Procedure

2-[4-Chloro-5-(4-fluorophenyl)thieno[2,3-d]pyrimidin-2-yl]ethanol (150 mg, 0.0005 mol), triethylamine (0.214 mL, 0.00154 mol) and 4-(methoxymethyl)piperidine hydrochloride (0.091 g, 0.00055 mol) were dissolved in ethanol (5 mL) and warmed to 55° C. for 2 hrs. The reaction was then poured over ice and extracted with DCM. The organics were dried by passage through a PTFE frit and concentrated in vacuo to give 2-[5-(4-fluorophenyl)-4-[4-(methoxymethyl)-1-piperidyl]thieno[2,3-d]pyrimidin-2-yl]ethanol (180 mg). LCMS RT=4.33 min. M+1=402.

Workup

additionThe reaction was then poured over ice
extractionextracted with DCM
dry with materialThe organics were dried by passage through a PTFE frit
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-40586b447d03404bb64a2d94f6cbb240
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09290511B2

Reaction notes

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