Ammonium Chloride → HCID 178422381, compound

HRID 450584Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:10]3[C:17]([CH3:18])=[C:16]([C:19]#[N:20])[S:15][C:11]=3[N:12]=[CH:13][N:14]=2)=[C:4]([O:21][CH:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)[CH:3]=1.[N-:28]=[N+:29]=[N-:30].[Na+].[Cl-].[NH4+]>CN(C=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:10]3[C:17]([CH3:18])=[C:16]([C:19]4[NH:30][N:29]=[N:28][N:20]=4)[S:15][C:11]=3[N:12]=[CH:13][N:14]=2)=[C:4]([O:21][CH:22]2[CH2:23][CH2:24][O:25][CH2:26][CH2:27]2)[CH:3]=1

Participants

Conditions

Temperature: 125 °C

Procedure

To a stirred solution of 4-(4-fluoro-2-(tetrahydro-2H-pyran-4-yloxy)phenylamino)-5-methylthieno[2,3-d]pyrimidine-6-carbonitrile (0.036 g, 0.093 mmol) in DMF (1.0 mL) was added sodium azide (0.012 g, 0.18 mmol) and ammonium chloride (0.01 g, 0.18 mmol) and the mixture heated at 125° C. for 1.5 hours. The solvent was concentrated in vacuo and the residue co-evaporated with toluene. The crude product was dissolved in 10% MeOH in DCM and the insoluble material removed by filtration. The residue was triturated from MeCN, the solid collected and dried under vacuum. The solid was purified by reverse phase preparative HPLC to give the product as beige solid after lyophilisation (0.021 g, 54%).

Workup

concentrationThe solvent was concentrated in vacuo
dissolutionThe crude product was dissolved in 10% MeOH in DCM
customthe insoluble material removed by filtration
customThe residue was triturated from MeCN
customthe solid collected
customdried under vacuum
customThe solid was purified by reverse phase preparative HPLC

Sources & evidence

ORD record: ord-0d913900e6054c02a556de39c54f0862
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08486953B2

Reaction notes

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