Tetrahydrofuran → HCID 58075466, compound

HRID 2370151Notes

Reaction equation

[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[CH2:10][O:9][CH:8]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[C:6]=2[N:7]=1.CC[N:21]([CH:25]([CH3:27])[CH3:26])C(C)C.[CH2:28]1COC[CH2:29]1>>[Cl:1][C:2]1[N:3]=[C:4]([NH:21][C@@H:25]([CH:26]2[CH2:29][CH2:28]2)[CH3:27])[C:5]2[CH2:10][O:9][CH:8]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[C:6]=2[N:7]=1

Participants

Reactant 3

HCID 8028Tetrahydrofuran

HCID 81531Diisopropylethylamine

HCID 580754962,4-Dichloro-7-(4-fluorophenyl)-5,7-dihydrofuro[3,4-d]pyrimidine

Product 1

HCID 58075466HCID 58075466, compoundYield 14.24%

Conditions

Temperature: 40 °C

Procedure

To a solution of 2,4-dichloro-7-(4-fluorophenyl)-5,7-dihydrofuro[3,4-d]pyrimidine (Preparation M) (150 mg, 0.526 mmol) in THF (2631 μL) was added (R)-1-cyclopropylethanamine, HCl (128 mg, 1.052 mmol) and DIEA (368 μL, 2.105 mmol). The mixture was heated at 40° C. for 2 h and stirred at RT overnight. The mixture was concentrated and purified by column chromatography on silica gel to give 2-chloro-N-((R)-1-cyclopropylethyl)-7-(4-fluorophenyl)-5,7-dihydrofuro[3,4-d]pyrimidin-4-amine (Preparation Mf) (25 mg, 0.075 mmol, 14.24% yield) as a mixture of 2 diasteriomers. LC-MS (M+H)+=334.1.

Workup

concentrationThe mixture was concentrated
custompurified by column chromatography on silica gel

Sources & evidence

ORD record: ord-bd0920259d3f427d9efe796ca4099a3c
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08710061B2

Reaction notes

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