Sodium hydride → HCID 21934607, compound

HRID 1241391Notes

Reaction equation

HRID 1241391 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[N:13]=[CH:12][N:11]=[C:10]([NH2:14])[CH:9]=2)[CH2:4][CH2:3]1.[H-].[Na+].Cl[C:18]1[S:19][C:20]([C:23]#[N:24])=[CH:21][N:22]=1>C1COCC1>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[N:13]=[CH:12][N:11]=[C:10]([NH:14][C:18]3[S:19][C:20]([C:23]#[N:24])=[CH:21][N:22]=3)[CH:9]=2)[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 14852222-Chlorothiazole-5-carbonitrileHCID 133941956-(4-Methylpiperazin-1-yl)pyrimidin-4-amine

Product 1

HCID 21934607HCID 21934607, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6-(4-Methyl-piperazin-1-yl)-pyrimidin-4-ylamine (97 mg, 0.50 mmol) was stirred in 2 mL anhydrous THF under N2. Sodium hydride (43 mg, 60% dispersion, 1.10 mmol) was added and after stirring for 30 minutes, 2-chloro-thiazole-5-carbonitrile (87 mg, 0.60 mmol). After LCMS indicated complete conversion, the reaction was quenched with MeOH, neutralized with 10% citric acid (aq). The resulting precipitate was filtered, washed with water and after air drying was washed with hexane. 1H-NMR (400 MHz, DMSO) 12.00 (1H, s), 8.42 (1H, s), 8.25 (1H, s), 6.21 (1H, s), 3.54 (m, 4H), 2.39 (m, 4H), 2.21 (s, 3H). M+1=302.3.

Workup

  1. customthe reaction was quenched with MeOH
  2. filtrationThe resulting precipitate was filtered
  3. washwashed with water
  4. customafter air drying
  5. washwas washed with hexane

Sources & evidence

ORD record
ord-a85bea9b24154f44bb5e938b7cf4fe12
Source dataset
uspto-grants-2006_10
Patent number
US07115597B2

Reaction notes

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