Tetrahydrofuran → HCID 178472328, compound

HRID 2279596Notes

Reaction equation

HRID 2279596 reaction equation
C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1COCC1.CCOC(/N=N/C(OCC)=O)=O.[CH2:37]([O:39][C:40](=[O:60])[C@@H:41]([OH:59])[CH2:42][CH2:43][C:44]1[C:45](O)=[N:46][C:47]([NH:51][CH:52]2[CH2:57][CH2:56][O:55][CH2:54][CH2:53]2)=[N:48][C:49]=1[OH:50])[CH3:38]>CN(C=O)C>[OH:50][C:49]1[C:44]2[CH2:43][CH2:42][C@H:41]([C:40]([O:39][CH2:37][CH3:38])=[O:60])[O:59][C:45]=2[N:46]=[C:47]([NH:51][CH:52]2[CH2:57][CH2:56][O:55][CH2:54][CH2:53]2)[N:48]=1

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 178472571HCID 178472571, compound

Product 1

HCID 178472328HCID 178472328, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A flask was charged with PPh3 (0.807 g, 3.08 mmol), anhydrous THF (20 mL) and DEAD (0.655 g, 3.08 mmol). The solution was stirred for 10 min under N2 then a solution of 400, THF (5 mL) and DMF (5 mL) was added and solution stirred 18 h. The solution was concentrated in vacuo to afford an orange oil. The crude product was purified by reverse phase chromatography (SP4 biotage 40M C18 using a C18 Biotage 40 samplet) and eluted with a MeCN/H2O gradient (0-60% MeCN) to afford a light yellow oil which solidified under high vacuum. The crude product was re-purified by SiO2 chromatography (SNAP 25) eluting with DCM/MeOH (95:5) to afford 0.42 g (60%) of Obtained (R)-ethyl 4-hydroxy-2-(tetrahydro-2H-pyran-4-ylamino)-6,7-dihydro-5H-pyrano[2,3-d]pyrimidine-7-carboxylate (402) as a clear oil: m/z (APCI-pos) M+1=324.0

Workup

  1. stirringsolution stirred 18 h
  2. concentrationThe solution was concentrated in vacuo
  3. customto afford an orange oil
  4. customThe crude product was purified by reverse phase chromatography (SP4 biotage 40M
  5. washeluted with a MeCN/H2O gradient (0-60% MeCN)
  6. customto afford a light yellow oil which
  7. customThe crude product was re-purified by SiO2 chromatography (SNAP 25)
  8. washeluting with DCM/MeOH (95:5)

Sources & evidence

ORD record
ord-27208ee5e3ac459a89e29bc2e34bb94f
Source dataset
uspto-grants-2015_09
Patent number
US09133187B2

Reaction notes

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