Diethyl Ether → 2-[(Cyclopropylmethyl-amino)-methyl]-3,5,7,8-tetrahydro-pyrano[4,3-d]pyrimidin-4-one

HRID 713395Notes

Reaction equation

HRID 713395 reaction equation
[CH:1]1([CH2:4][N:5]([CH2:13][C:14]2[NH:15][C:16](=[O:24])[C:17]3[CH2:23][O:22][CH2:21][CH2:20][C:18]=3[N:19]=2)C(=O)OC(C)(C)C)[CH2:3][CH2:2]1.C(OCC)C>Cl.O1CCOCC1>[CH:1]1([CH2:4][NH:5][CH2:13][C:14]2[NH:15][C:16](=[O:24])[C:17]3[CH2:23][O:22][CH2:21][CH2:20][C:18]=3[N:19]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 3283Diethyl EtherHCID 136627243tert-Butyl N-(cyclopropylmethyl)-N-[(4-oxo-4,5,7,8-tetrahydro-3H-pyrano[4,3-d]pyrimidin-2-yl)methyl]carbamate

Product 1

HCID 1362440742-[(Cyclopropylmethyl-amino)-methyl]-3,5,7,8-tetrahydro-pyrano[4,3-d]pyrimidin-4-oneYield 121.8%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

tert-butyl cyclopropylmethyl((4-oxo-4,5,7,8-tetrahydro-3H-pyrano[4,3-d]pyrimidin-2-yl)methyl)carbamate (5.639 g, 16.81 mmol) was dissolved in 4 N HCl in dioxane (40 mL) and stirred at room temperature after approximately 5 min a white suspension formed and the reaction was allowed to stir overnight. 100 mL diethyl ether was added and the reaction mixture was filtered, washed with diethyl ether (2×25 mL) and dried in vacuo to yield the title compound as a white solid (4.819 g).

Workup

  1. customformed
  2. stirringto stir overnight
  3. filtrationthe reaction mixture was filtered
  4. washwashed with diethyl ether (2×25 mL)
  5. customdried in vacuo

Sources & evidence

ORD record
ord-abd6badb1f7041fd95650acc9883a40e
Source dataset
uspto-grants-2015_11
Patent number
US09181266B2

Reaction notes

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