Hydrochloric Acid → HCID 71727580, compound

HRID 1774205Notes

Reaction equation

HRID 1774205 reaction equation
[Si]([O:8][CH2:9][CH2:10][C@@H:11]([N:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH:31]=[CH:30][N:29]=[C:28]([NH:32][CH:33]3[CH2:38][CH2:37][O:36][CH2:35][CH2:34]3)[N:27]=2)=[CH:22][C:21]1=[O:39])[C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([F:19])[CH:13]=1)(C(C)(C)C)(C)C.Cl>C(Cl)(Cl)Cl.O1CCOCC1>[Cl:18][C:15]1[CH:16]=[CH:17][C:12]([C@H:11]([N:20]2[CH:25]=[CH:24][C:23]([C:26]3[CH:31]=[CH:30][N:29]=[C:28]([NH:32][CH:33]4[CH2:34][CH2:35][O:36][CH2:37][CH2:38]4)[N:27]=3)=[CH:22][C:21]2=[O:39])[CH2:10][CH2:9][OH:8])=[CH:13][C:14]=1[F:19]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86696705HCID 86696705, compound

Product 1

HCID 71727580HCID 71727580, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 312751,4-DioxaneSolvent

Procedure

(R)-1-(3-(tert-Butyldimethylsilyloxy)-1-(4-chloro-3-fluorophenyl)propyl)-4-(2-((tetrahydro-2H-pyran-4-yl)amino)pyrimidin-4-yl)pyridin-2(1H)-one (0.056 g, 0.098 mmol) was dissolved in chloroform (1 mL), and 4M HCl in dioxane was added. After agitating for 30 minutes, the mixture was evaporated and dried in vacuo to give (R)-1-(1-(4-chloro-3-fluorophenyl)-3-hydroxypropyl)-4-(2-((tetrahydro-2H-pyran-4-yl)amino)pyrimidin-4-yl)pyridin-2(1H)-one (0.045 g, 0.098 mmol, quantitative yield) as a solid. 1H NMR (400 MHz, CDCl3) δ 9.22 (d, J=5.0 Hz, 1H), 8.37 (d, J=5.0 Hz, 1H), 7.42 (t, J=5.0 Hz, 1H), 7.36 (s, 1H), 7.28-7.10 (m, 4H), 6.77 (d, J=5.0 Hz, 1H), 6.45 (m, 1H), 4.25 (br s, 1H), 4.20-4.00 (m, 2H), 3.80-3.42 (m, 9H), 2.55 (m, 1H), 2.20 (m, 1H), 2.02 (m, 2H), 1.82 (m, 2H); m/z (APCI-pos) M+1=459.0.

Workup

  1. customthe mixture was evaporated
  2. customdried in vacuo

Sources & evidence

ORD record
ord-6223a1ef1bbc492682664bbd02556f19
Source dataset
uspto-grants-2016_02
Patent number
US09259470B2

Reaction notes

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