4-Methylbenzoyl Chloride → HCID 178425840, compound

HRID 473992Notes

Reaction equation

HRID 473992 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[N:14]=[C:13]([NH:15][C:16]3[NH:20][N:19]=[C:18]([CH3:21])[CH:17]=3)[CH:12]=[C:11]([N:22]3[CH2:25][CH2:24][CH2:23]3)[N:10]=2)=[CH:4][CH:3]=1.[C:26]1([CH3:35])[CH:31]=[CH:30][C:29]([C:32](Cl)=[O:33])=[CH:28][CH:27]=1>N1C=CC=CC=1>[CH3:21][C:18]1[CH:17]=[C:16]([NH:15][C:13]2[CH:12]=[C:11]([N:22]3[CH2:23][CH2:24][CH2:25]3)[N:10]=[C:9]([S:8][C:5]3[CH:6]=[CH:7][C:2]([NH:1][C:32](=[O:33])[C:29]4[CH:30]=[CH:31][C:26]([CH3:35])=[CH:27][CH:28]=4)=[CH:3][CH:4]=3)[N:14]=2)[NH:20][N:19]=1

Participants

4

Reactant 2

HCID 134054-Methylbenzoyl ChlorideHCID 178428240HCID 178428240, compound

Product 1

HCID 178425840HCID 178425840, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-(4-Aminophenylthio)-6-(azetidin-1-yl)-N-(3-methyl-1H-pyrazol-5-yl)pyrimidin-4-amine (200 mg, 0.57 mmol) was taken up in pyridine (2 mL) and p-toluoyl chloride (0.187 mL, 1.42 mmol) was added dropwise at room temperature. After 15 minutes the reaction mixture was concentrated in vacuo and the residue taken up in methanol (3 mL). Sodium methoxide (25% w/w solution in MeOH, 1 mL) was added and the resulting cloudy solution stirred at room temperature for 15 minutes. The reaction mixture was purified directly by chromatography (silica, 5-100% EtOAc-petrol gradient elution) to give the title compound (91 mg, 34%) as a white solid. 1H NMR: (400 MHz, DMSO) 1.99 (3H, brs), 2.33 (2H, qn), 2.40 (3H, s), 3.88 (4H, t), 5.38 (1H, brs), 5.59 (1H, vbrs), 7.36 (2H, d), 7.53 (2H, d), 7.87 (2H, d), 7:91 (2H, d), 9.20 (1H, brs), 10.36 (1H, s), 11.66 (1H, brs); MS (ES+) 472.

Workup

  1. concentrationAfter 15 minutes the reaction mixture was concentrated in vacuo
  2. additionSodium methoxide (25% w/w solution in MeOH, 1 mL) was added
  3. customThe reaction mixture was purified directly by chromatography (silica, 5-100% EtOAc-petrol gradient elution)

Sources & evidence

ORD record
ord-4b2935426eb145be861a2c295585f8cd
Source dataset
uspto-grants-2014_01
Patent number
US08637511B2

Reaction notes

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