HCID 52206516, compound → 2-Chloro-7-methyl-8-(3-methylbutyl)-7,8-dihydropteridin-6(5H)-one

HRID 530093Notes

Reaction equation

HRID 530093 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([N:8]([CH2:15][CH2:16][CH:17]([CH3:19])[CH3:18])[C@H:9]([C:11](OC)=[O:12])[CH3:10])[C:5]([N+:20]([O-])=O)=[CH:4][N:3]=1>[Fe].C(O)(=O)C>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[NH:20][C:11](=[O:12])[CH:9]([CH3:10])[N:8]([CH2:15][CH2:16][CH:17]([CH3:19])[CH3:18])[C:6]=2[N:7]=1

Participants

4

Reactant 1

HCID 52206516HCID 52206516, compound

Product 1

HCID 426095712-Chloro-7-methyl-8-(3-methylbutyl)-7,8-dihydropteridin-6(5H)-oneYield 61%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of methyl N-(2-chloro-5-nitropyrimidin-4-yl)-N-(3-methylbutyl)alaninate (16.2 g, 49 mmol), iron powder (6.9 g, 123 mmol) and glacial acetic acid (165 mL) was heated at 60° C. for 2 h. The reaction mixture was then filtered while hot over celite and washed with hot acetic acid (40 mL) followed by ethyl acetate (250 mL). The filtrate after evaporation was taken up in ethyl acetate and washed two times with aq. saturated sodium bicarbonate solution followed by brine. It was dried over sodium sulfate and evaporated. The residue was triturated with hot isopropyl ether to give titled product (yield: 61%). 1HNMR (300 MHz, CDCl3): δ 0.92-1.01 (m, 7H), 1.43-1.75 (m, 5H), 3.01-3.20 (m, 1H), 4.10-4.25 (m, 2H), 7.63 (s, 1H), 9.13 (s, 1H).

Workup

  1. filtrationThe reaction mixture was then filtered while hot over celite
  2. washwashed with hot acetic acid (40 mL)
  3. customThe filtrate after evaporation
  4. washwashed two times with aq. saturated sodium bicarbonate solution
  5. dry with materialIt was dried over sodium sulfate
  6. customevaporated
  7. customThe residue was triturated with hot isopropyl ether

Sources & evidence

ORD record
ord-357cbdf2089e427d938093f310f859a7
Source dataset
uspto-grants-2016_05
Patent number
US09351974B2

Reaction notes

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