Sodium Iodide → HCID 59239258, compound

HRID 1697940Notes

Reaction equation

HRID 1697940 reaction equation
Cl.[CH2:2]([NH:4][C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:15]=[C:16]([N:24]3[CH2:29][CH2:28][O:27][CH2:26][C@@H:25]3[CH3:30])[C:17]3[CH2:23][CH2:22][NH:21][CH2:20][C:18]=3[N:19]=2)=[CH:10][CH:9]=1)=[O:6])[CH3:3].CC1C=CC(S(O[CH2:42][C@@H:43]2[CH2:47][O:46][C:45]([CH3:49])([CH3:48])[O:44]2)(=O)=O)=CC=1.[I-].[Na+].CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:48][C:45]1([CH3:49])[O:44][C@H:43]([CH2:42][N:21]2[CH2:22][CH2:23][C:17]3[C:16]([N:24]4[CH2:29][CH2:28][O:27][CH2:26][C@@H:25]4[CH3:30])=[N:15][C:14]([C:11]4[CH:10]=[CH:9][C:8]([NH:7][C:5]([NH:4][CH2:2][CH3:3])=[O:6])=[CH:13][CH:12]=4)=[N:19][C:18]=3[CH2:20]2)[CH2:47][O:46]1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 81531DiisopropylethylamineHCID 2723760(S)-(+)-2,2-Dimethyl-1,3-dioxolan-4-ylmethyl p-ToluenesulfonateHCID 66687899HCID 66687899, compound

Product 1

HCID 59239258HCID 59239258, compoundYield 64.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (S)-1-ethyl-3-(4-(4-(3-methylmorpholino)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl)urea hydrochloride (jk) (270 mg, 0.69 mmol), (S)-(2,2-dimethyl-1,3-dioxolan-4-yl)methyl 4-methylbenzenesulfonate (377 mg, 132 mmol), sodium iodide (104 mg, 0.69 mmol), DIPEA (0.48 mL, 2.8 mmol), and DMF (1.0 mL) was heated at 110° C. for 22 h. The mixture was partitioned between ethyl acetate and sat. NaHCO3. The phases were separated, and the aqueous layer extracted with ethyl acetate (2×). The combined organic phases were dried over Na2SO4, filtered and concentrated onto Celite, and the residue chromatographed: ISCO 12 g column 0-20% IPA in DCM to afford 228 mg (64%) of the title compound jz as an off-white solid: LC-MS: m/z=+511 (M+H)+.

Workup

  1. customThe mixture was partitioned between ethyl acetate and sat. NaHCO3
  2. customThe phases were separated
  3. extractionthe aqueous layer extracted with ethyl acetate (2×)
  4. dry with materialThe combined organic phases were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated onto Celite
  7. customthe residue chromatographed

Sources & evidence

ORD record
ord-690ee3ca650643539b8a1ab8eb17d2c5
Source dataset
uspto-grants-2012_04
Patent number
US08163763B2

Reaction notes

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