KRS_038_001 (Experiment #58)

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Synthesis of N-(4-methylpyridin-2-yl)-4-(o-tolyl)-thiazol-2-amine

Link to HIRAC

Reaction Scheme

Reaction Table

Reagents	KRS_033	KRS_026	EtOH
Equivalents	1	1	-
Molecular weight (g/mol)	213.07	167.23	-
Mass (grams)	0.098	0.077	-
Number of moles (mmol)	0.460	0.460	-
Volume (mL)	-	-	2.5

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Procedure

1. Dissolved KRS_033 in EtOH
2. Addition of KRS_026
3. Heated to reflux (78 °C, reached temp at 11:45), clear solution upon heating with a precipitate forming within minutes.

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4. TLC at 13:45 with 10% EtOAc in petroleum benzine with KMnO₄ still a little starting material so left on for longer.

   

5. TLC at 15:30 - exactly the same, work up.

   

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5. Reaction cooled to room temperature and left stirring until 15:40.
6. Poured over ice water (~10 mL)
7. pH adjusted to ~ 10 with a saturated aqueous solution of Na2CO3 (starting pH was 1) to precipitate the product. A very cream solid formed
8. The precipitate was collected via vacuum filtration and washed with ice water (2 x 10 mL) followed by cold hexane (2 x 10 mL) and dried under vacuum for 5 minutes.

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9. ¹H NMR indicated product

NMR Raw Data KRS_038_001_1.zip

Yield

Product is a cream solid Experimental: 96 mg Theoretical: 129 mg Percentage: 74%

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Raw and processed IR, NMR (1H, 13C, COSY, HSQC and HMBC) and HRMS