Dibutyltin oxide → HCID 178490276, compound

HRID 216126Notes

Reaction equation

HRID 216126 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([C:9]2[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=2)[C:12]#[N:13])[CH:6]=[C:5]([NH:17][CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)[N:4]=1.C[Si]([N:32]=[N+:33]=[N-:34])(C)C.C([Sn](=O)CCCC)CCC>C1(C)C=CC=CC=1>[CH3:27][O:26][C:23]1[CH:22]=[CH:21][C:20]([CH2:19][CH2:18][NH:17][C:5]2[CH:6]=[C:7]([C:9]3[CH:16]=[CH:15][CH:14]=[C:11]([C:12]4[NH:34][N:33]=[N:32][N:13]=4)[CH:10]=3)[N:8]=[C:3]([O:2][CH3:1])[N:4]=2)=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 61221Dibutyltin oxideHCID 78378AzidotrimethylsilaneHCID 11660493HCID 11660493, compound

Product 1

HCID 178490276HCID 178490276, compoundYield 45.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 3-{2-methoxy-6-[2-(4-methoxy-phenyl)-ethylamino]-pyrimidin-4-yl}-benzonitrile [0.12 g, 0.33 mmol, Example 35(t)], trimethylsilylazide (0.22 mL, 1.65 mmol) and dibutyltinoxide (41 mg, 0.16 mmol) in toluene (5 mL) is heated to 95° C. for 6 hours. The reaction mixture is concentrated, and partitioned between water and ethyl acetate. The aqueous phase solution is acidified with dilute hydrochloric acid to pH, 3.0, and extracted with ethyl acetate. The extracts are dried over magnesium sulfate, filtered and concentrated. The residue is subjected to chromatography on silica gel eluting with 5% MeOH in DCM to afford [2-(4-methoxy-phenyl)-ethyl]-{2-methoxy-6-[3-(1H-tetrazol-5-yl)-phenyl]-pyrimidin-4-yl}-amine [60 mg, 45%, Example 24(a)]. LCMS: RT=2.65 minutes, MS: 404 (M+H).

Workup

  1. concentrationThe reaction mixture is concentrated
  2. custompartitioned between water and ethyl acetate
  3. extraction3.0, and extracted with ethyl acetate
  4. dry with materialThe extracts are dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e99c660c519c491f959fd9e92cd4e0e7
Source dataset
uspto-grants-2012_06
Patent number
US08193183B2

Reaction notes

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