Methanol → N-benzyl-6-chloropyrimidin-4-amine

HRID 877919Notes

Reaction equation

HRID 877919 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:9][C:10]1[CH:15]=[C:14](Cl)[N:13]=[CH:12][N:11]=1.C(N(CC)CC)C.CO>C(Cl)Cl>[CH2:1]([NH:8][C:14]1[CH:15]=[C:10]([Cl:9])[N:11]=[CH:12][N:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 7504BenzylamineHCID 8471TriethylamineHCID 709434,6-Dichloropyrimidine

Product 1

HCID 3771857N-benzyl-6-chloropyrimidin-4-amineYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Benzyl amine (0.697ml, 6.76 mmol) was added to 4,6-dichloropyrimidine (1.0 g, 6.76 mmol) neat causing a vigorous reaction and color change. The reaction was slowly diluted with methylene chloride resulting in a white precipitate. 1 ml of triethyl amine was added and TLC indicated conversion to product (5% MeOH:methylene chloride). The reaction was loaded directly onto a silica and purified (eluent:2% MeOH:methylene chloride) giving 1.17 g (5.32 mmol) of 12 as a yellow wax in 79% yield.

Workup

  1. customa vigorous reaction and color change
  2. custompurified (eluent:2% MeOH:methylene chloride)

Sources & evidence

ORD record
ord-d397d170f0eb44e6ab27f80cc507db59
Source dataset
uspto-grants-2015_03
Patent number
US08987454B2

Reaction notes

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