Ammonia → HCID 57794964, compound

HRID 2099573Notes

Reaction equation

HRID 2099573 reaction equation
CS([C:4]1[N:9]=[C:8]([CH:10]([C:24]2[CH:25]=[C:26]([CH:29]=[CH:30][CH:31]=2)[C:27]#[N:28])[CH:11]([C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)[C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)[CH:7]=[CH:6][N:5]=1)=O.[NH3:32]>>[NH2:32][C:4]1[N:9]=[C:8]([CH:10]([C:24]2[CH:25]=[C:26]([CH:29]=[CH:30][CH:31]=2)[C:27]#[N:28])[CH:11]([C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)[C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)[CH:7]=[CH:6][N:5]=1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 68801297HCID 68801297, compound

Product 1

HCID 57794964HCID 57794964, compound

Conditions

Temperature
100 °C

Procedure

The solution of diastereomeric mixture of (±)-3-{1-[2-(methylsulfinyl)pyrimidin-4-yl]-2,2-dipyridin-3-ylethyl}benzonitrile (0.11 g, 0.25 mmol) in NH3 saturated DMSO(2 mL) was heated to 100 ° C. in microwave for 2 h. The mixture was concentrated and the residue was purified by silica gel chromatography (5% MeOH in CH2Cl2) to give (±)-3-[1-(2-aminopyrimidin-4-yl)-2,2-dipyridin-3-ylethyl]benzonitrile. 1H-NMR (500 MHz, DMSO-d6) δ 8.68 (d, 1H, J=1.5), 8.60 (d, 1H, J=1.5), 8.29 (d, 1H, J=4.6), 8.23 (d, 1H, J=4.6), 8.00 (d, 1H, J=4.8), 7.95 (s, 1H), 7.90(t, 2H, J=9.4), 7.80(d, 1H, J=8.0), 7.55 (d, 1H, J=7.6), 7.40 (t, 1H, J=7.8), 7.25(dd, 1H, J=7.8, 4.6), 7.19(dd, 1H, J=8.0, 4.6), 6.67(d, 1H, J=5.1), 6.54(s,2H), 5.25 (d, 1H, J=12.5), 5.20 (d, 1H, J=12.4). LRMS m/z (M+H) Calcd: 379.4, found: 379.2.

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was purified by silica gel chromatography (5% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-2fac349f47344fb88ccb0e198b5ab8d3
Source dataset
uspto-grants-2009_08
Patent number
US07569589B2

Reaction notes

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