Hydrochloric Acid → HCID 178489739, compound

HRID 656631Notes

Reaction equation

HRID 656631 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[N:17]=[C:16]([NH:18][O:19]C3CCCCO3)[C:15]3[C:14]([CH3:26])=[N:13][C:12]([NH2:27])=[N:11][C:10]=3[CH2:9]2)=[C:4]([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([O:34][CH3:35])[N:29]=2)[CH:3]=1.Cl>O1CCOCC1>[NH2:27][C:12]1[N:13]=[C:14]([CH3:26])[C:15]2=[C:10]([CH2:9][C@H:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][C:4]=3[C:28]3[CH:33]=[CH:32][CH:31]=[C:30]([O:34][CH3:35])[N:29]=3)[NH:17]/[C:16]/2=[N:18]\[OH:19])[N:11]=1

Participants

4

Reactant 2

HCID 313Hydrochloric Acid2×HCID 57999257(7R)-7-(4-fluoro-2-(6-methoxypyridin-2-yl)phenyl)-4-methyl-5-(tetrahydro-2H-pyran-2-yloxyamino)-7,8-dihydropyrido[4,3-d]pyrimidin-2-amine

Product 1

HCID 178489739HCID 178489739, compoundYield 63.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

(7R)-7-(4-fluoro-2-(6-methoxypyridin-2-yl)phenyl)-4-methyl-5-(tetrahydro-2H-pyran-2-yloxyamino)-7,8-dihydropyrido[4,3-d]pyrimidin-2-amine (0.891 g, 1.86 mmol) was dissolved in 10 mL of dioxane. 4M of HCl in dioxane (1.86 mL, 7.45 mmol) was then added slowly to the above stirred solution. After all the HCl was added, a yellow solid was formed at the bottom of the reaction flask. The deprotection was allowed to go for 30 minutes, then the supernatant was decanted. Dichloromethane was added to wash the solid, then it was decanted. This process was repeated a few times. No product was found in the dioxane and dichloromethane washes. The solid product was then purified on flash column chromatography, SiO2, gradient 2-15% methanol/chloroform to give 0.404 g of product, 63.5% yield over 2 steps. MS (ES) [M+H] calc'd for C20H19FN6O2, 395. found, 395.3. 1H NMR (400 MHz, METHANOL-d4) δ 2.60 (s, 3H), 3.09-3.19 (m, 1H), 3.29-3.34 (m, 1H), 3.91 (s, 3H), 5.45 (br. s., 1H), 6.82 (d, J=8.34 Hz, 1H), 7.16 (d, J=6.57 Hz, 1H), 7.19-7.30 (m, 2H), 7.55 (dd, J=8.59, 5.56 Hz, 1H), 7.79 (dd, J=8.34, 7.33 Hz, 1H).

Workup

  1. customa yellow solid was formed at the bottom of the reaction flask
  2. customthe supernatant was decanted
  3. additionDichloromethane was added
  4. washto wash the solid
  5. customit was decanted
  6. customThe solid product was then purified on flash column chromatography, SiO2, gradient 2-15% methanol/chloroform

Sources & evidence

ORD record
ord-2eff5ec1a5d34c5db18b1d1fc567c6dc
Source dataset
uspto-grants-2011_12
Patent number
US08071766B2

Reaction notes

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