Hydrochloric Acid → 2-Chloro-4-morpholinothieno[3,2-d]pyrimidine-6-carbonitrile

HRID 2262282Notes

Reaction equation

HRID 2262282 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[C:5]2[S:10][C:9](I)=[CH:8][C:6]=2[N:7]=1.[C:18]([Cu])#[N:19].Cl>N1C=CC=CC=1>[Cl:1][C:2]1[N:3]=[C:4]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[C:5]2[S:10][C:9]([C:18]#[N:19])=[CH:8][C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 595930614-(2-Chloro-6-iodothieno[3,2-d]pyrimidin-4-yl)morpholineHCID 178418546HCID 178418546, compound

Product 1

HCID 866184522-Chloro-4-morpholinothieno[3,2-d]pyrimidine-6-carbonitrileYield 24.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 2-chloro-6-iodo-4-morpholinothieno[3,2-d]pyrimidine 19 from Example 12 (0.2 g, 0.5 mmol) and CuCN (50 mg, 0.6 mmol) in pyridine (1 mL) was heated at 115° C. for 2 h then cooled to room temperature and stirred 18 h. The reaction was poured into 1 M HCl and ice and the aqueous layer was extracted with CH2Cl2. The product was purified by silica gel chromatography (0-75% EtOAc in hexane) to provide 2-chloro-4-morpholinothieno[3,2-d]pyrimidine-6-carbonitrile (35 mg).

Workup

  1. extractionthe aqueous layer was extracted with CH2Cl2
  2. customThe product was purified by silica gel chromatography (0-75% EtOAc in hexane)

Sources & evidence

ORD record
ord-65f3fa68465f465e8f53235a46764ff2
Source dataset
uspto-grants-2010_12
Patent number
US07846929B2

Reaction notes

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