Methylamine → HCID 18442526, compound

HRID 458685Notes

Reaction equation

HRID 458685 reaction equation
[CH2:1]([O:8][C:9]1[C:14](=[O:15])[N:13]([CH2:16][CH2:17][C:18]([O:20]C)=O)[C:12](S(C)(=O)=O)=[N:11][C:10]=1[C:26]([O-:28])=[O:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:29][NH2:30].O1[CH2:35][CH2:34]CC1>>[CH2:1]([O:8][C:9]1[C:14](=[O:15])[N:13]2[CH2:16][CH2:17][C:18](=[O:20])[N:30]([CH3:29])[C:12]2=[N:11][C:10]=1[C:26]([O:28][CH2:34][CH3:35])=[O:27])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 6329MethylamineHCID 8028Tetrahydrofuran2×HCID 18442515HCID 18442515, compound

Product 1

HCID 18442526HCID 18442526, compoundYield 77%

Conditions

Temperature
22 °C

Procedure

A solution of ethyl intermediate 9, 5-benzyloxy-1-(2-methoxycarbonylethyl)-2-methylsulfonyl-6-oxo-1,6-dihydro-pyrimidine-4-carboxylate, (0.594 g, 1.35 mmol) in tetrahydrofuran (10 ml) was treated with 10 ml (20 mmol) of a 2M solution of methylamine in tetrahydrofuran and the resulting mixture stirred at 22° C. for 1 h. The solvent was then evaporated in vacuo and the residue diluted with toluene and heated under reflux for 2.5 h. The reaction mixture was then diluted with ethyl acetate washed successively with saturated sodium bicarbonate and brine then dried over anhydrous magnesium sulfate. Evaporation of the solvent followed by chromatography on silica gel (elution gradient of ethyl acetate 0–20% in toluene) gave 0.374 g (77% yield) of the title ester as white crystals; mp 121° C. (ethyl acetate/hexane). 1HNMR 400 MHz (CDCl3) δ (ppm): 1.31 (3H, t, J=7.1 Hz, CH3), 2.82 (2H, t, J=7.0 Hz, CH2), 3.42 (3H, s, NCH3), 4.27 (2H, t, J=7.0 Hz, CH2), 4.33 (2H, q, J=7.1 Hz, OCH2), 5.20 (2H, s, OCH2), 7.36 (3H, m, aromatics), 7.47 (2H, m, aromatics). Anal. Calcd for C18H19N3O5: C, 60.49; H, 5.35; N, 11.75. Found: C, 60.12; H, 5.04; N, 11.49.

Workup

  1. customThe solvent was then evaporated in vacuo
  2. additionthe residue diluted with toluene
  3. temperatureheated
  4. temperatureunder reflux for 2.5 h
  5. additionThe reaction mixture was then diluted with ethyl acetate
  6. washwashed successively with saturated sodium bicarbonate and brine
  7. dry with materialthen dried over anhydrous magnesium sulfate
  8. customEvaporation of the solvent

Sources & evidence

ORD record
ord-c74ad31a2fc64f94a9b780ba667970f1
Source dataset
uspto-grants-2007_03
Patent number
US07192948B2

Reaction notes

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