Dimethylformamide → HCID 90994180, compound

HRID 1836971Notes

Reaction equation

CN(C=O)C.O=[C:7]1[NH:12][C:11]([CH2:13][O:14][CH2:15][C:16]([O:18][CH2:19][CH2:20][CH2:21][CH3:22])=[O:17])=[N:10][C:9]2[S:23][C:24]3[CH2:29][CH2:28][CH2:27][CH2:26][C:25]=3[C:8]1=2.S(Cl)([Cl:32])=O>>[Cl:32][C:7]1[C:8]2[C:25]3[CH2:26][CH2:27][CH2:28][CH2:29][C:24]=3[S:23][C:9]=2[N:10]=[C:11]([CH2:13][O:14][CH2:15][C:16]([O:18][CH2:19][CH2:20][CH2:21][CH3:22])=[O:17])[N:12]=1

Participants

Reactant 3

HCID 6228Dimethylformamide

HCID 24386Thionyl Chloride

HCID 91234921HCID 91234921, compound

Product 1

HCID 90994180HCID 90994180, compound

Procedure

1.7 g of sodium hydride (50% suspension) are added to a solution of 5.0 g of “AB” and 2.8 g of butyl glycolate in 100 ml of THF, and the mixture is refluxed for 3 hours. The solvent is removed, and the mixture is subjected to conventional work-up, giving 5.0 g of butyl (4-oxo-3,4,5,6,7,8-hexahydrobenzo[4,5]thieno[2,3-d]pyrimidin-2-ylmethoxy)acetate (“AC”). 1 ml of DMF is added to a solution of 5.0 g of “AC” in 50 ml of thionyl chloride, and the mixture is stirred at 45° for 2 hours. After the solvent has been removed, the mixture is subjected to conventional work-up, giving 4.5 g of butyl (4-chloro-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-2-ylmethoxy)acetate (“AD”).

Workup

customAfter the solvent has been removed

Sources & evidence

ORD record: ord-cadf77229dcb48c78e3019395d2d4da5
Source dataset: uspto-grants-2004_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06780867B2

Reaction notes

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