3-Amino-1-propanol → 3-[(2-Chloro-5-methyl-4-pyrimidinyl)amino]-1-propanol

HRID 2235948Notes

Reaction equation

HRID 2235948 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([CH3:9])=[CH:4][N:3]=1.[NH2:10][CH2:11][CH2:12][CH2:13][OH:14].C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[Cl:1][C:2]1[N:7]=[C:6]([NH:10][CH2:11][CH2:12][CH2:13][OH:14])[C:5]([CH3:9])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 90863-Amino-1-propanolHCID 10340Sodium CarbonateHCID 74508Pyrimidine, 2,4-dichloro-5-methyl-

Product 1

HCID 593004463-[(2-Chloro-5-methyl-4-pyrimidinyl)amino]-1-propanolYield 99%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2,4-dichloro-5-methylpyrimidine (8.00 g, 49.1 mmol) and 3-amino-1-propanol (4.50 mL, 58.9 mmol) in ethanol (200 mL) was added sodium carbonate (26.0 g, 245 mmol). The solution was vigorously stirred at rt for 24 h. The mixture was filtered over Celite® and the filtrate concentrated under reduced pressure. The resulting solid was triturated with Et2O to give the product as a white solid (9.80 g, 99%). 1H NMR (400 MHz, CDCl3) δ 1.86 (qt, 2H), 2.00 (s, 3H), 3.55 (t, 2H), 3.64 (t, 2H), 4.92 (broad, 2H), 7.68 (s, 1H).

Workup

  1. filtrationThe mixture was filtered over Celite®
  2. concentrationthe filtrate concentrated under reduced pressure
  3. customThe resulting solid was triturated with Et2O

Sources & evidence

ORD record
ord-522ea5aec6e14a68ab564a89daffd90e
Source dataset
uspto-grants-2010_05
Patent number
US07714004B2

Reaction notes

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