Methanol → HCID 86705493, compound

HRID 2279490Notes

Reaction equation

HRID 2279490 reaction equation
[OH:1][C@H:2]1[CH2:6][CH2:5][C@H:4]([NH:7][C:8]2[N:9]=[CH:10][C:11]3[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14][C:12]=3[N:13]=2)[CH2:3]1.CO.Cl.O1CCOCC1>C(Cl)Cl>[NH3:7].[N:13]1[C:12]2[CH2:14][NH:15][CH2:16][CH2:17][C:11]=2[CH:10]=[N:9][C:8]=1[NH:7][C@H:4]1[CH2:5][CH2:6][C@H:2]([OH:1])[CH2:3]1

Participants

6

Reactant 3

HCID 887MethanolHCID 204431481,4-Dioxane hydrochlorideHCID 86705494HCID 86705494, compound

Product 2

HCID 222AmmoniaHCID 86705493HCID 86705493, compoundYield 165.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 166 (10.85 g, 21.09 mmol), DCM (100 mL) and MeOH (10 mL) was added HCl/dioxane (26.36 mL, 105.4 mmol, 4N solution in dioxane) and the reaction was stirred for 18 h. The solution was concentrated to afford a red oil. To the residue was added DCM/methanolic NH3 (100 mL, 9:1, 7N) and the mixture sonicated for 5 min. The filtrate was concentrated to afford a thick red oil. The crude product was purified by SiO2 chromatography (Biotage 40 M) eluting with DCM/7N methanolic:NH3 (4:1 then 9:1 solution) to afford 4.1 g (80%) of (1S,3S)-3-(5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-ylamino)cyclopentanol (168) as a light brown oil: MS m/z (APCI-pos) M+1=235.2.

Workup

  1. concentrationThe solution was concentrated
  2. customto afford a red oil
  3. customthe mixture sonicated for 5 min
  4. concentrationThe filtrate was concentrated
  5. customto afford a thick red oil
  6. customThe crude product was purified by SiO2 chromatography (Biotage 40 M)
  7. washeluting with DCM/7N methanolic

Sources & evidence

ORD record
ord-b4aeecea86084ebd9c1656dc971fbe95
Source dataset
uspto-grants-2015_09
Patent number
US09133187B2

Reaction notes

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