1-Butanol → n4-benzyl-6-chloropyrimidine-4,5-diamine

HRID 1678020Notes

Reaction equation

HRID 1678020 reaction equation
[NH2:1][C:2]1[C:3]([Cl:9])=[N:4][CH:5]=[N:6][C:7]=1Cl.C(O)CCC.C(N(CC)CC)C.[CH2:22]([NH2:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>>[NH2:1][C:2]1[C:7]([NH:29][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[N:6][CH:5]=[N:4][C:3]=1[Cl:9]

Participants

5

Reactant 4

HCID 2631-ButanolHCID 7504BenzylamineHCID 8471TriethylamineHCID 794345-Amino-4,6-dichloropyrimidine

Product 1

HCID 258596n4-benzyl-6-chloropyrimidine-4,5-diamineYield 96.1%

Conditions

Temperature
100 °C

Procedure

To a solution of 5-amino-4,6-dichloropyrimidine (8.4 g, 0.051 mol) in 1-butanol (50.0 mL, 0.547 mol) was added triethylamine (12 mL, 0.084 mol) and benzylamine (17 mL, 0.15 mol), and the mixture was heated at 100° C. for 3 hours. The reaction was cooled at 0 C, filtered and washed with ethanol. The residue was dissolved in CH2Cl2 and washed with saturated aqueous NaHCO3, and concentrated. The residue was triturated in diethyl ether to obtain 11.5 g (96%) of a light brown solid.

Workup

  1. temperatureThe reaction was cooled at 0 C
  2. filtrationfiltered
  3. washwashed with ethanol
  4. dissolutionThe residue was dissolved in CH2Cl2
  5. washwashed with saturated aqueous NaHCO3
  6. concentrationconcentrated
  7. customThe residue was triturated in diethyl ether

Sources & evidence

ORD record
ord-c7d457982e814fb2bbf7800b66899f33
Source dataset
uspto-grants-2011_08
Patent number
US08008307B2

Reaction notes

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