Triethylamine → 2-{[(3,5-Dichloropyridin-4-yl)methyl]sulfanyl}-6-methylpyrimidin-4-amine

HRID 577167Notes

Reaction equation

HRID 577167 reaction equation
Br.Br[CH2:3][C:4]1[C:9]([Cl:10])=[CH:8][N:7]=[CH:6][C:5]=1[Cl:11].[NH2:12][C:13]1[CH:18]=[C:17]([CH3:19])[N:16]=[C:15]([SH:20])[N:14]=1.C(N(CC)CC)C>CCO>[Cl:11][C:5]1[CH:6]=[N:7][CH:8]=[C:9]([Cl:10])[C:4]=1[CH2:3][S:20][C:15]1[N:14]=[C:13]([NH2:12])[CH:18]=[C:17]([CH3:19])[N:16]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 668153104-(Bromomethyl)-3,5-dichloropyridine hydrobromideHCID 178428717HCID 178428717, compound

Product 1

HCID 595893712-{[(3,5-Dichloropyridin-4-yl)methyl]sulfanyl}-6-methylpyrimidin-4-amineYield 92%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-(bromomethyl)-3,5-dichloropyridine hydrobromide (2.9 g, 10.5 mmol), 4-amino-6-methylpyrimidine-2-thiol (1.0 g, 7.1 mmol), and triethylamine (3 mL, 21.5 mmol) in absolute EtOH (80 mL) was stirred at room temperature overnight. The mixture was evaporated, co-evaporated with EtOAc (20 mL), and dried in vacuo. The solid residue was treated with water (150 mL). The solid product was recovered by filtration, washed with water (2×25 mL), diethyl ether (2×25 mL), and hexanes (2×25 mL), and dried in vacuo, affording the title compound (1.9 g, 92% yield); 1H NMR (400 MHz, DMSO-d6): δ 2.29 (s, 3H), 4.78 (s, 2H), 6.29 (s, 1H), 8.45 (s (br), 2H), 8.69 (s, 2H); M+ 302.

Workup

  1. customThe mixture was evaporated
  2. customdried in vacuo
  3. additionThe solid residue was treated with water (150 mL)
  4. filtrationThe solid product was recovered by filtration
  5. washwashed with water (2×25 mL), diethyl ether (2×25 mL), and hexanes (2×25 mL)
  6. customdried in vacuo

Sources & evidence

ORD record
ord-a819c6c2f1a545bf9273ea97bf6f1589
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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