Potassium Phosphate, Tribasic → HCID 117600741, compound

HRID 931655Notes

Reaction equation

HRID 931655 reaction equation
P([O-])([O-])([O-])=O.[K+].[K+].[K+].Cl[C:10]1[N:15]=[CH:14][C:13]2[O:16][C:17]3[C:22]([C@@:23]4([CH2:28][CH2:27][O:26][C:25]([NH2:29])=[N:24]4)[C:12]=2[CH:11]=1)=[CH:21][C:20]([NH2:30])=[CH:19][CH:18]=3.[O:31]1[CH2:36][CH2:35][CH:34]=[C:33](B2OC(C)(C)C(C)(C)O2)[CH2:32]1>O1CCOCC1.O>[O:31]1[CH2:36][CH2:35][CH:34]=[C:33]([C:10]2[N:15]=[CH:14][C:13]3[O:16][C:17]4[C:22]([C@@:23]5([CH2:28][CH2:27][O:26][C:25]([NH2:29])=[N:24]5)[C:12]=3[CH:11]=2)=[CH:21][C:20]([NH2:30])=[CH:19][CH:18]=4)[CH2:32]1

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 158366332-(5,6-dihydro-2H-pyran-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 117600968HCID 117600968, compound

Product 1

HCID 117600741HCID 117600741, compoundYield 74.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

A microwave reaction vessel was charged with potassium phosphate (tribasic) (0.670 g, 3.16 mmol), (S)-3-chloro-5′,6′-dihydrospiro[chromeno[2,3-c]pyridine-5,4′-[1,3]oxazine]-2′,7-diamine (0.2 g, 0.631 mmol), and 2-(5,6-dihydro-2H-pyran-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.398 g, 1.894 mmol) in dioxane (4 ml) and water (2 ml). The vessel was capped and the solution was purged with nitrogen for 10 minutes. Next, bis[di-tert-butyl(4 dimethylaminophenyl)phosphine]dichloropalladium(II) (0.022 g, 0.032 mmol) was added and the vessel was sealed. The reaction mixture was stirred and heated in a Initiator microwave reactor (Personal Chemistry, Biotage AB, Inc., Upssala, Sweden) at 120° C. for 35 minutes. The reaction was poured into water and the mixture was extracted with EtOAc. The combined organic extracts were washed with saturated aqueous sodium chloride and dried over sodium sulfate. The solution was filtered and concentrated in vacuo to give the crude material. The crude material was purified by silica gel chromatography by eluting with 20:1 solution of DCM to a 2M solution of NH3 in MeOH, to provide (S)-3-(5,6-dihydro-2H-pyran-3-yl)-5′,6′-dihydrospiro[chromeno[2,3-c]pyridine-5,4′-[1,3]oxazine]-2′,7-diamine (0.172 g, 0.472 mmol, 74.8% yield) as an off-white solid.

Workup

  1. customA microwave reaction vessel
  2. customThe vessel was capped
  3. customthe solution was purged with nitrogen for 10 minutes
  4. customthe vessel was sealed
  5. extractionthe mixture was extracted with EtOAc
  6. washThe combined organic extracts were washed with saturated aqueous sodium chloride
  7. dry with materialdried over sodium sulfate
  8. filtrationThe solution was filtered
  9. concentrationconcentrated in vacuo
  10. customto give the crude material
  11. customThe crude material was purified by silica gel chromatography
  12. washby eluting with 20:1 solution of DCM to a 2M solution of NH3 in MeOH

Sources & evidence

ORD record
ord-88ac2182441e477a82c5a58f0b6c73d9
Source dataset
uspto-grants-2016_03
Patent number
US09296759B2

Reaction notes

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