Acetamide → N-[5-phenyl-2-[4-(2-pyrrolidin-1-ylethoxymethyl)-1-piperidyl]thieno[2,3-d]pyrimidin-6-yl]acetamide

HRID 928587Notes

Reaction equation

Br[C:2]1[S:25][C:5]2[N:6]=[C:7]([N:10]3[CH2:15][CH2:14][CH:13]([CH2:16][O:17][CH2:18][CH2:19][N:20]4[CH2:24][CH2:23][CH2:22][CH2:21]4)[CH2:12][CH2:11]3)[N:8]=[CH:9][C:4]=2[C:3]=1[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[C:32]([NH2:35])(=[O:34])[CH3:33].C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>C(Cl)Cl.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CC#N>[C:26]1([C:3]2[C:4]3[CH:9]=[N:8][C:7]([N:10]4[CH2:15][CH2:14][CH:13]([CH2:16][O:17][CH2:18][CH2:19][N:20]5[CH2:24][CH2:23][CH2:22][CH2:21]5)[CH2:12][CH2:11]4)=[N:6][C:5]=3[S:25][C:2]=2[NH:35][C:32](=[O:34])[CH3:33])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

Conditions

Temperature: 150 °C

Procedure

6-Bromo-5-phenyl-2-[4-(2-pyrrolidin-1-ylethoxymethyl)-1-piperidyl]thieno[2,3-d]pyrimidine (0.125 g, 0.25 mmol), acetamide (0.022 g, 0.37 mmol), cesium carbonate (0.163 g, 0.5 mmol), xantphos (0.022 g, mol %), Pd2(dba)3 (0.010 g, 5 mol %) and MeCN (2 mL) were combined and heated to 150° C. for 30 minutes. The reaction was diluted with DCM (10 mL), washed with water (10 mL), passed through a hydrophobic frit and concentrated at reduced pressure. The resulting residue was purified by basic prep HPLC to afford N-[5-phenyl-2-[4-(2-pyrrolidin-1-ylethoxymethyl)-1-piperidyl]thieno[2,3-d]pyrimidin-6-yl]acetamide (22 mg). LCMS [M+H]+=480.2

Workup

washwashed with water (10 mL)
concentrationconcentrated at reduced pressure
customThe resulting residue was purified by basic prep HPLC

Sources & evidence

ORD record: ord-12275e2945da450886c7df3a6417cdbb
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09290511B2

Reaction notes

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