Isopropylamine → 4'-Cyclopropylmethyl-N2'-isopropyl-N2-pyridin-4-yl-[4,5']bipyrimidinyl-2,2'-diamine

HRID 1397159Notes

Reaction equation

HRID 1397159 reaction equation
[CH:1]1([CH2:4][C:5]2[C:10]([C:11]3[CH:16]=[CH:15][N:14]=[C:13]([NH:17][C:18]4[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=4)[N:12]=3)=[CH:9][N:8]=[C:7](SC)[N:6]=2)[CH2:3][CH2:2]1.[CH:26]([NH2:29])([CH3:28])[CH3:27]>CS(C)=O>[CH:1]1([CH2:4][C:5]2[C:10]([C:11]3[CH:16]=[CH:15][N:14]=[C:13]([NH:17][C:18]4[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=4)[N:12]=3)=[CH:9][N:8]=[C:7]([NH:29][CH:26]([CH3:28])[CH3:27])[N:6]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 679838584'-(Cyclopropylmethyl)-2'-(methylsulfanyl)-N-pyridin-4-yl-4,5'-bipyrimidin-2-amine

Product 1

HCID 679834244'-Cyclopropylmethyl-N2'-isopropyl-N2-pyridin-4-yl-[4,5']bipyrimidinyl-2,2'-diamineYield 39.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 4′-(cyclopropylmethyl)-2′-(methylsulfanyl)-N-pyridin-4-yl-4,5′-bipyrimidin-2-amine (11) (35 mg, 0.096 mmol) in DMSO (1 mL), isopropylamine (24.55 μl, 0.287 mmol) was added and the reaction was microwaved for 20 minutes at 160° C. The crude product was purified by reverse-phase HPLC [30-100% organic phase over 15 minutes] followed by Biotage™ silica gel chromatography [10 g SNAP column, 100% DCM to 10% MeOH/DCM] to afford the title compound as a pale-yellow solid (13.67 mg, 39.6% yield). 1H NMR (400 MHz, MeOD) δ ppm 0.04-0.17 (m, 2 H) 0.31-0.50 (m, 2 H) 0.97-1.17 (m, 1 H) 1.27 (d, J=6.57 Hz, 6 H) 2.88 (d, J=7.07 Hz, 2 H) 4.22 (ddd, J=13.01, 6.44, 6.32 Hz, 1 H) 7.10 (d, J=5.05 Hz, 1 H) 7.84 (d, J=7.07 Hz, 2 H) 8.30 (d, J=6.57 Hz, 2 H) 8.42 (s, 1 H) 8.55 (d, J=5.05 Hz, 1 H). HRMS (ES+) for C20 H23N7.H+ [MH+]: calcd, 362.2093. found, 362.2083. UV-LC: 100% UV purity at 254/214 nm; tR=3.39 minutes over 7.75 minutes.

Workup

  1. customthe reaction was microwaved for 20 minutes at 160° C
  2. customThe crude product was purified by reverse-phase HPLC [30-100% organic phase over 15 minutes]

Sources & evidence

ORD record
ord-8078757c4fa847aa84967f08ce6d3999
Source dataset
uspto-grants-2014_12
Patent number
US08901147B2

Reaction notes

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