4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-amine → Tert-butyl 6-(3-aminopyridin-4-yl)-2-methylpyrimidin-4-ylcarbamate

HRID 69953Notes

Reaction equation

HRID 69953 reaction equation
Cl[C:2]1[N:7]=[C:6]([CH3:8])[N:5]=[C:4]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH:3]=1.CC1(C)C(C)(C)OB([C:25]2[CH:30]=[CH:29][N:28]=[CH:27][C:26]=2[NH2:31])O1>COCCOC.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[NH2:31][C:26]1[CH:27]=[N:28][CH:29]=[CH:30][C:25]=1[C:2]1[N:7]=[C:6]([CH3:8])[N:5]=[C:4]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH:3]=1

Participants

5

Reactant 2

HCID 497604144-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-amineHCID 86669200tert-Butyl (6-chloro-2-methylpyrimidin-4-yl)carbamate

Product 1

HCID 69047460Tert-butyl 6-(3-aminopyridin-4-yl)-2-methylpyrimidin-4-ylcarbamateYield 26%

Reagents, catalysts & solvents 2

HCID 178418807HCID 178418807, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

Method 26 was followed using tert-butyl 6-chloro-2-methylpyrimidin-4-ylcarbamate (1.0 equiv.), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-amine (3.0 equiv.), Pd(dppf)Cl2-DCM (0.10 equiv.) in DME/2M Na2CO3 (3:1, 0.07M) at 80° C. for 30 min. Purification via SiO2 column chromatography eluting with EtOAc afforded tert-butyl 6-(3-aminopyridin-4-yl)-2-methylpyrimidin-4-ylcarbamate in 26% yield. LCMS (m/z): 302.1 (MH+); LC Rt=2.23 min.

Workup

  1. customat 80° C.
  2. customfor 30 min
  3. customPurification via SiO2 column chromatography
  4. washeluting with EtOAc

Sources & evidence

ORD record
ord-b5f110fa30ac47bb948392878b7e81e1
Source dataset
uspto-grants-2014_09
Patent number
US08822497B2

Reaction notes

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