Hydrochloric Acid → (R)-2-(tetrahydro-2H-pyran-4-ylamino)-6,7-dihydro-5H-pyrano[2,3-d]pyrimidine-7-carboxylic acid

HRID 2279598Notes

Reaction equation

HRID 2279598 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8]2[N:9]=[CH:10][C:11]3[CH2:17][CH2:16][C@H:15]([C:18]([O:20]CC)=[O:19])[O:14][C:12]=3[N:13]=2)[CH2:3][CH2:2]1.O[Li].O.Cl.O1CCOCC1>O.C1COCC1>[O:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8]2[N:9]=[CH:10][C:11]3[CH2:17][CH2:16][C@H:15]([C:18]([OH:20])=[O:19])[O:14][C:12]=3[N:13]=2)[CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 168937Lithium hydroxide, monohydrateHCID 86705579(R)-ethyl 2-(tetrahydro-2H-pyran-4-ylamino)-6,7-dihydro-5H-pyrano[2,3-d]pyrimidine-7-carboxylate

Product 1

HCID 86705581(R)-2-(tetrahydro-2H-pyran-4-ylamino)-6,7-dihydro-5H-pyrano[2,3-d]pyrimidine-7-carboxylic acidYield 109.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 406 (0.310 g, 1.01 mmol), THF (5 mL), LiOH.H2O (0.0508 g, 1.21 mmol) and water (1 mL) was stirred for 3 h. To the solution was added 4N HCl in dioxane (0.303 mL, 1.21 mmol) and concentrated to afford 0.31 g (95%) of (R)-2-(tetrahydro-2H-pyran-4-ylamino)-6,7-dihydro-5H-pyrano[2,3-d]pyrimidine-7-carboxylic acid (408) which was used without further purification: MS m/z (APCI-pos) M+1=280.1.

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-ea01e1627dc14b68a808da462c7eafe3
Source dataset
uspto-grants-2015_09
Patent number
US09133187B2

Reaction notes

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