Boron trifluoride etherate → HCID 178489731, compound

HRID 656588Notes

Reaction equation

HRID 656588 reaction equation
[OH:1][C@H:2]1[C@@H:6]([OH:7])[CH:5](OC)[O:4][C@@H:3]1[CH2:10][O:11]/[N:12]=[C:13]1\[NH:14][C@@H:15]([C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:26]=2[C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([O:38][CH3:39])[N:33]=2)[CH2:16][C:17]2[N:18]=[C:19]([NH2:24])[N:20]=[C:21]([CH3:23])[C:22]\1=2.[SiH](CC)(CC)CC.B(F)(F)F.CCOCC>C(Cl)Cl>[OH:1][C@H:2]1[C@@H:6]([OH:7])[CH2:5][O:4][C@@H:3]1[CH2:10][O:11]/[N:12]=[C:13]1\[NH:14][C@@H:15]([C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:26]=2[C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([O:38][CH3:39])[N:33]=2)[CH2:16][C:17]2[N:18]=[C:19]([NH2:24])[N:20]=[C:21]([CH3:23])[C:22]\1=2

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 12052TriethylsilaneHCID 178489732HCID 178489732, compound

Product 1

HCID 178489731HCID 178489731, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R,Z)-2-amino-7-(4-fluoro-2-(6-methoxypyridin-2-yl)phenyl)-4-methyl-7,8-dihydropyrido[4,3-d]pyrimidin-5(6H)-one O-((2R,3S,4R)-3,4-dihydroxy-5-methoxytetrahydrofuran-2-yl)methyl oxime (10.5 mg, 0.02 mmol) in CH2Cl2 (1 mL) was added Et3SiH (16 μL, 0.05 mmol) and BF3.Et2O (8.0 μL, 0.05 mmol) at 0° C. under N2 atmosphere. The reaction mixture was stirred overnight at r.t. and poured on crushed ice. The resultant slurry was extracted with CH2Cl2 and washed with brine. Work-up and purification by Preparative LCMS afforded the title compound (3.0 mg, 30%) as light brown solid. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.50 (s, 3H) 2.77 (dd, J=16.04, 6.95 Hz, 1H) 3.00 (dd, J=16.04, 5.18 Hz, 1H) 3.15-3.26 (m, 2H) 3.35-3.42 (m, 2H) 3.83 (s, 3H) 3.85-3.94 (m, 2H) 4.38-4.41 (m, 1H) 4.93-5.13 (m, 1H) 6.82 (d, J=9.09 Hz, 1H) 7.16 (d, J=7.07 Hz, 1H) 7.21-7.30 (m, 2H) 7.45 (dd, J=8.46, 5.94 Hz, 1H) 7.86 (dd, J=8.34, 7.33 Hz, 1H). MS (ES) [M+H] calculated for C25H28FN6O5, 511.51. found 511.20.

Workup

  1. additionpoured
  2. customon crushed ice
  3. extractionThe resultant slurry was extracted with CH2Cl2
  4. washwashed with brine
  5. custompurification by Preparative LCMS

Sources & evidence

ORD record
ord-44daa88a8a444d29b84956c06905d21e
Source dataset
uspto-grants-2011_12
Patent number
US08071766B2

Reaction notes

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