Tetrahydro-4H-pyran-4-one → HCID 86670132, compound

HRID 1631748Notes

Reaction equation

HRID 1631748 reaction equation
[Cl:1][C:2]1[N:11]=[CH:10][C:9]2[NH:8][CH2:7][C@@H:6]3[CH2:12][O:13][CH2:14][CH2:15][N:5]3[C:4]=2[N:3]=1.[O:16]1[CH2:21][CH2:20][C:19](=O)[CH2:18][CH2:17]1>[Na].C(Cl)Cl.[Ti](Cl)(Cl)(Cl)Cl>[Cl:1][C:2]1[N:11]=[CH:10][C:9]2[N:8]([CH:19]3[CH2:20][CH2:21][O:16][CH2:17][CH2:18]3)[CH2:7][C@@H:6]3[CH2:12][O:13][CH2:14][CH2:15][N:5]3[C:4]=2[N:3]=1

Participants

6

Reactant 2

HCID 121599Tetrahydro-4H-pyran-4-oneHCID 86670088(R)-2-chloro-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine

Product 1

HCID 86670132HCID 86670132, compound

Reagents, catalysts & solvents 3

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent2×HCID 5360545SodiumSolvent

Procedure

The title compound was prepared in a manner similar to PREPARATION x63 using (R)-2-chloro-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine (PREPARATION x2, 250 mg, 1.103 mmol), dihydro-2H-pyran-4-(3H)-one (110 mg, 1.103 mmol), titanium(IV) chloride in CH2Cl2 (1M, 2.427 mL, 2.427 mmol) and sodium triacetoxyhydroborate (514 mg, 2.427 mmol) in CH2Cl2 (8 mL) (10 mg, 3%). ESI-MS m/z [M+H]+ calc'd for C14H19ClN4O2, 311.13. found 311.2.

Sources & evidence

ORD record
ord-be6f36b85cab44188f98002a3e50611c
Source dataset
uspto-grants-2014_07
Patent number
US08791107B2

Reaction notes

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