C-(5-methylfuran-2-yl)-C-(3-methyloxetan-3-yl)methylamine → HCID 178425502, compound

HRID 1528177Notes

Reaction equation

HRID 1528177 reaction equation
[OH:1][C:2]1[C:7]([NH:8][C:9]2[C:10](=O)[C:11](=[O:15])[C:12]=2[O:13]C)=[CH:6][N:5]=[CH:4][N:3]=1.[CH3:17][C:18]1[O:22][C:21]([CH:23]([NH2:29])[C:24]2([CH3:28])[CH2:27][O:26][CH2:25]2)=[CH:20][CH:19]=1>CO>[OH:1][C:2]1[C:7]([NH:8][C:9]2[C:12](=[O:13])[C:11](=[O:15])[C:10]=2[NH:29][CH:23]([C:21]2[O:22][C:18]([CH3:17])=[CH:19][CH:20]=2)[C:24]2([CH3:28])[CH2:25][O:26][CH2:27]2)=[CH:6][N:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 89525357C-(5-methylfuran-2-yl)-C-(3-methyloxetan-3-yl)methylamineHCID 178493686HCID 178493686, compound

Product 1

HCID 178425502HCID 178425502, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 300 mg (1.36 mmol, 1 eq) of 3-(4-hydroxypyrimidin-5-ylamino)-4-methoxycyclobut-3-ene-1,2-dione and 504 mg (2.78 mmol, 2 eq) of C-(5-methylfuran-2-yl)-C-(3-methyloxetan-3-yl)methylamine in 25 ml of methanol was heated at 50° C. for 22 hours. The reaction medium was filtered and the insoluble material was washed with methanol and with diethyl ether. 0.36 g of product was obtained in the form of a white solid. Yield=72%, HPLC purity=97.81%, Mp=281° C. (degradation).

Workup

  1. filtrationThe reaction medium was filtered
  2. washthe insoluble material was washed with methanol and with diethyl ether

Sources & evidence

ORD record
ord-ad52b0f45f1e458e8c11c2cc65409c60
Source dataset
uspto-grants-2015_07
Patent number
US09090596B2

Reaction notes

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