Diethylamine → HCID 178464160, compound

HRID 577033Notes

Reaction equation

HRID 577033 reaction equation
[CH2:1]([NH:3][CH2:4][CH3:5])[CH3:2].C[Mg+].[Br-].[Cl:9][C:10]1[C:11]([CH2:18][S:19][C:20]2[N:25]=C(O)C=C(C)[N:21]=2)=[C:12]([CH:15]=[CH:16][CH:17]=1)[C:13]#[N:14].[CH2:28]1[CH2:32][O:31][CH2:30][CH2:29]1>>[Cl:9][C:10]1[C:11]([CH2:18][S:19][C:20]2[N:21]=[C:30]([OH:31])[CH:29]=[C:28]([CH3:32])[N:25]=2)=[C:12]([C:13](=[NH:14])[N:3]([CH2:4][CH3:5])[CH2:1][CH3:2])[CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 4

HCID 8021DiethylamineHCID 8028TetrahydrofuranHCID 178418689HCID 178418689, compoundHCID 178429454HCID 178429454, compound

Product 1

HCID 178464160HCID 178464160, compoundYield 68%

Conditions

Temperature
40 °C

Procedure

In a 100 mL round bottom flask, diethylamine (0.31 mL, 3.0 mmol) was added into the solution of MeMgBr (0.90 mL, 3 mmol) in THF (20 mL). The resulting mixture was stirred at 40° C. for 1 hour, followed by addition of 3-chloro-2-{[(4-hydroxy-6-methylpyrimidin-2-yl)sulfanyl]methyl}benzonitrile (292 mg, 1.0 mmol). After another 1.5 hours, the solvent was removed under vacuum. The crude product was purified by CombiFlash (0 to 20% MeOH in DCM) to provide the title compound as a grey-yellow solid (200 mg, 68% yield); 1H NMR (400 MHz, DMSO-d6): δ 1.17 (t, 6H), 2.28 (s, 3H), 3.31 (q, 4H), 4.60-4.80 (m, 2H), 6.03 (br, 1H), 7.57 (m, 2H), 7.88 (d, 1H); M+ 365.

Workup

  1. waitAfter another 1.5 hours
  2. customthe solvent was removed under vacuum
  3. customThe crude product was purified by CombiFlash (0 to 20% MeOH in DCM)

Sources & evidence

ORD record
ord-8dc1df42e04745c0a3de85e87a453876
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

Loading…