4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-amine → 6-(3-aminopyridin-4-yl)-N,N-di-BOC-2-(methylthio)pyrimidin-4-amine

HRID 69952Notes

Reaction equation

HRID 69952 reaction equation
Cl[C:2]1[N:7]=[C:6]([S:8][CH3:9])[N:5]=[C:4]([N:10]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:3]=1.CC1(C)C(C)(C)OB([C:33]2[CH:38]=[CH:37][N:36]=[CH:35][C:34]=2[NH2:39])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>[NH2:39][C:34]1[CH:35]=[N:36][CH:37]=[CH:38][C:33]=1[C:2]1[N:7]=[C:6]([S:8][CH3:9])[N:5]=[C:4]([N:10]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:3]=1

Participants

5

Reactant 2

HCID 497604144-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-amineHCID 86669199HCID 86669199, compound

Product 1

HCID 690443816-(3-aminopyridin-4-yl)-N,N-di-BOC-2-(methylthio)pyrimidin-4-amineYield 32%

Reagents, catalysts & solvents 2

HCID 178418807HCID 178418807, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

Method 26 was followed using 6-chloro-N,N-di-BOC-2-(methyl-thio)pyrimidin-4-amine (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 (0.07M) at 90° C. for 30 min. Purification via SiO2 column chromatography eluting with EtOAc and hexanes (1:1) afforded 6-(3-aminopyridin-4-yl)-N,N-di-BOC-2-(methyl-thio)pyrimidin-4-amine in 32% yield. LCMS (m/z): 434.2 (MH+); LC Rt=3.56 min.

Workup

  1. customat 90° C.
  2. customfor 30 min
  3. customPurification via SiO2 column chromatography
  4. washeluting with EtOAc and hexanes (1:1)

Sources & evidence

ORD record
ord-370a64d3a18d470188e1a0013fe53baa
Source dataset
uspto-grants-2014_09
Patent number
US08822497B2

Reaction notes

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