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

HRID 713392Notes

Reaction equation

Cl[CH2:2][C:3]1[NH:4][C:5](=[O:13])[C:6]2[CH2:12][O:11][CH2:10][CH2:9][C:7]=2[N:8]=1.[CH:14]1([CH2:17][NH2:18])[CH2:16][CH2:15]1>C(O)C>[CH:14]1([CH2:17][NH:18][CH2:2][C:3]2[NH:4][C:5](=[O:13])[C:6]3[CH2:12][O:11][CH2:10][CH2:9][C:7]=3[N:8]=2)[CH2:16][CH2:15]1

Participants

Conditions

Temperature: 45 °C

Procedure

To a solution of 2-chloromethyl-3,5,7,8-tetrahydro-pyrano[4,3-d]pyrimidin-4-one (1.0 g, 4.98 mmol) in ethanol (30 mL) was added cyclopropylmethylamine (2.13 g, 29.9 mmol). The mixture was then heated at 45° C. for 60 hours. The reaction was then stopped and the mixture was concentrated under high vacuum for 24 h. The remaining semi-solid was subjected to column chromatography (Silica gel, 0-10% methanol in dichloromethane) to give 2-[(cyclopropylmethyl-amino)-methyl]-3,5,7,8-tetrahydro-pyrano[4,3-d]pyrimidin-4-one as a light brown solid (540 mg, 2.30 mmol, 46% yield) that was directly used in the next step. m/z=236.4 (M+H).

Workup

concentrationthe mixture was concentrated under high vacuum for 24 h

Sources & evidence

ORD record: ord-346542a5bb554818b2963044e6289c20
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181266B2

Reaction notes

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