Sodium Hydroxide → [4-(2,4-Dimethyl-thiazol-5-yl)-pyrimidin-2-yl]-(4-pyridin-4-ylmethyl-phenyl)-amine

HRID 47211Notes

Reaction equation

HRID 47211 reaction equation
[CH3:1][C:2]1[N:6]=[C:5]([CH3:7])[S:4][C:3]=1/[CH:8]=[CH:9]/[C:10](N(C)C)=O.Cl.[N:16]1[CH:21]=[CH:20][C:19]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([NH:29][C:30]([NH2:32])=[NH:31])=[CH:25][CH:24]=2)=[CH:18][CH:17]=1.[OH-].[Na+]>O(CCO)C>[CH3:7][C:5]1[S:4][C:3]([C:8]2[CH:9]=[CH:10][N:32]=[C:30]([NH:29][C:26]3[CH:25]=[CH:24][C:23]([CH2:22][C:19]4[CH:18]=[CH:17][N:16]=[CH:21][CH:20]=4)=[CH:28][CH:27]=3)[N:31]=2)=[C:2]([CH3:1])[N:6]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 916216443-Dimethylamino-1-(2,4-dimethyl-thiazol-5-yl)-propenoneHCID 178479368HCID 178479368, compound

Product 1

HCID 10384731[4-(2,4-Dimethyl-thiazol-5-yl)-pyrimidin-2-yl]-(4-pyridin-4-ylmethyl-phenyl)-amine

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

A mixture of 3-dimethylamino-1-(2,4-dimethyl-thiazol-5-yl)-propenone (1 mmol, 0.21 g) and N-(4-pyridin-4-ylmethyl-phenyl)-guanidine hydrochloride (2 mmol, 0.40 mg) in 2-methoxylethanol was treated with NaOH (40 mg). The reaction mixture was allowed to heat at reflux for 2 d. The solvent was evaporated and the residue was crystallised from EtOAc/MeOH to afford the title compound as an orange solid. 1H-NMR (300 MHz, d6-DMSO) δ3.00 (s, 3H, CH3), 3.02 (s, 3H, CH3), 4.29 (s, 2H, CH2), 7.44 (d, 1H, J=5.5 Hz, pyrimidinyl-H), 7.56 (m, 2H, Ph-H), 7.61 (m, 2H, Ar—H), 8.09 (m, 2H, Ph-H), 8.82 (m, 2H, Ar—H), 8.87 (d, 1H, J=5.5 Hz, pyrimidinyl-H). DE MALDI-TOF MS: {M+H}+=377.52 (C21H19N5S requires 373.48).

Workup

  1. temperatureto heat
  2. temperatureat reflux for 2 d
  3. customThe solvent was evaporated
  4. customthe residue was crystallised from EtOAc/MeOH

Sources & evidence

ORD record
ord-d7623985c2dc4bd287dedaf3612075de
Source dataset
uspto-grants-2004_03
Patent number
US06699854B2

Reaction notes

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