Tributyltin azide → HCID 57636126, compound

HRID 216174Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH2:9][CH2:10][NH:11][C:12]1[N:17]=[C:16]([CH3:18])[N:15]=[C:14]([C:19]2[CH:20]=[C:21]([C:25]([CH3:29])([CH3:28])[C:26]#[N:27])[CH:22]=[CH:23][CH:24]=2)[CH:13]=1.[N:30]([Sn](CCCC)(CCCC)CCCC)=[N+:31]=[N-:32]>FC(F)(F)C1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH2:9][CH2:10][NH:11][C:12]1[CH:13]=[C:14]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([CH3:29])([C:26]3[N:30]=[N:31][NH:32][N:27]=3)[CH3:28])[CH:20]=2)[N:15]=[C:16]([CH3:18])[N:17]=1

Participants

Conditions

Temperature: 180 °C

Procedure

To a solution of 2-(3-{6-[2-(2,4-dichloro-phenyl)-ethylamino]-2-methyl-pyrimidin-4-yl}-phenyl)-2-methyl-propionitrile [50 mg, 0.11 mmol, Intermediate (67)] in α, α, α-trifluorotoluene (2 mL) is added azidotributyltin (0.251 mL, 0.88 mmol) and heated in microwave oven at 180° C. for 1.5 hours. Reaction mixture is concentrated and purified via silica gel chromatography eluting with 20 to 100% EtOAc in heptane to give [2-(2,4-dichloro-phenyl)-ethyl]-(2-methyl-6-{3-[1-methyl-1-(2H-tetrazol-5-yl)-ethyl]-phenyl}-pyrimidin-4-yl)-amine as a solid, which is treated with 1M hydrogen chloride in ether affording [2-(2,4-dichloro-phenyl)-ethyl]-(2-methyl-6-{3-[1-methyl-1-(2H-tetrazol-5-yl)-ethyl]-phenyl}-pyrimidin-4-yl)-amine hydrochloride [47 mg, 80%, Example 47] as a solid. LC/MS: RT=2.47 minutes, MS: 484 (M+H). 1H NMR [300 MHz, (CD3)2SO]: □8.64 (1H, br s), 7.3-7.8 (7H, m), 6.56 (1H, s), 3.98 (3H, s), 3.64 (2H, m), 3 (2H, m), 1.8 (6H, s). IC50=0.4 nM

Workup

customReaction mixture
concentrationis concentrated
custompurified via silica gel chromatography
washeluting with 20 to 100% EtOAc in heptane

Sources & evidence

ORD record: ord-3cc7ff80c51c45c28d537c919ff3f1d4
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08193183B2

Reaction notes

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