Sodium Iodide → {2-[4-(4-Chlorophenyl)piperazin-1-yl]-7-methoxythieno[3,2-d]pyrimidin-4-yl}propylamine

HRID 1806001Notes

Reaction equation

Br[C:2]1[C:6]2[N:7]=[C:8]([N:15]3[CH2:20][CH2:19][N:18]([C:21]4[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=4)[CH2:17][CH2:16]3)[N:9]=[C:10]([CH2:11][CH2:12][CH2:13][NH2:14])[C:5]=2[S:4][CH:3]=1.[CH3:28][O-:29].[Na+].[I-].[Na+]>CO.[Cu]=O>[Cl:27][C:24]1[CH:25]=[CH:26][C:21]([N:18]2[CH2:19][CH2:20][N:15]([C:8]3[N:9]=[C:10]([CH2:11][CH2:12][CH2:13][NH2:14])[C:5]4[S:4][CH:3]=[C:2]([O:29][CH3:28])[C:6]=4[N:7]=3)[CH2:16][CH2:17]2)=[CH:22][CH:23]=1

Participants

Conditions

Temperature: 160 °C

Procedure

2.00 g (4.28 mmol) of {7-bromo-2-[4-(4-chlorophenyl)piperazin-1-yl]thieno[3,2-d]pyrimidin-4-yl}propylamine (VII) is placed in 15 mL of methanol and cooled to some extent. First 0.995 g (18.42 mmol) of sodium methoxide, then 0.187 g (2.36 mmol) of copper (II) oxide, and 0.040 g (0.27 mmol) of sodium iodide are added. The reaction mixture is heated to 160° C. in the microwave for 0.75 hours. Then it is suction filtered through silica gel and the mother liquor is concentrated by evaporation. The residue is dissolved and any insoluble matter is removed by suction filtering. Further purification is carried out by preparative HPLC. 0.23 g of product VIII (20%) is obtained.

Workup

temperaturecooled to some extent
filtrationfiltered through silica gel
concentrationthe mother liquor is concentrated by evaporation
dissolutionThe residue is dissolved
customany insoluble matter is removed by suction
filtrationfiltering
customFurther purification

Sources & evidence

ORD record: ord-c43f6b0993e04514b16bf08776b8f2b9
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08354531B2

Reaction notes

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