Methyl iodide → HCID 86665101, compound

HRID 1038816Notes

Reaction equation

HRID 1038816 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([N:11]2[CH2:16][CH2:15][N:14]3[C:17]([CH2:20][NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[N:18][CH:19]=[C:13]3[CH2:12]2)[C:5]2[O:10][CH:9]=[CH:8][C:6]=2[N:7]=1.Cl[C:30]1N=C(Cl)C2OC=CC=2N=1.[H-].[Na+].CI.[NH4+].[Cl-]>C1COCC1>[Cl:1][C:2]1[N:3]=[C:4]([N:11]2[CH2:16][CH2:15][N:14]3[C:17]([CH2:20][N:21]([CH3:30])[C:22](=[O:28])[O:23][C:24]([CH3:25])([CH3:27])[CH3:26])=[N:18][CH:19]=[C:13]3[CH2:12]2)[C:5]2[O:10][CH:9]=[CH:8][C:6]=2[N:7]=1

Participants

7

Reactant 5

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 457899682,4-Dichlorofuro[3,2-D]pyrimidineHCID 86665102Carbamic acid, N-[[7-(2-chlorofuro[3,2-d]pyrimidin-4-yl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyrazin-3-yl]methyl]-, 1,1-dimethylethyl ester

Product 1

HCID 86665101HCID 86665101, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of tert-butyl (7-(2-chlorofuro[3,2-d]pyrimidin-4-yl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyrazin-3-yl)methylcarbamate (0.300 g, 0.741 mmol, prepared using A from 2,4-dichlorofuro[3,2-d]pyrimidine [Arkpharm] with Preparation #G.1) in THF (10 mL) was cooled to about 0° C. To the flask was added NaH (60 wt % dispersion in mineral oil, 0.036 g, 1.5 mmol) and the mixture was stirred for about 0.5 h at about 0° C. To the mixture was added MeI (0.21 g, 1.48 mmol) and the mixture was stirred for about 30 min. Saturated NH4Cl (15 mL) was added then the mixture was extracted with EtOAc (3×20 mL). The organic extracts were combined then dried over anhydrous Na2SO4 then filtered. The filtrate was concentrated under reduced pressure to give tert-butyl (7-(2-chlorofuro[3,2-d]pyrimidin-4-yl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyrazin-3-yl)methyl(methyl)carbamate (0.255 g, 82%): LC/MS (Table 2, Method h) Rt=1.93 min; MS m/z: 419 (M+H)+.

Workup

  1. stirringthe mixture was stirred for about 30 min
  2. extractionthe mixture was extracted with EtOAc (3×20 mL)
  3. dry with materialThe organic extracts were combined then dried over anhydrous Na2SO4
  4. filtrationthen filtered
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-4e6b32a84f8a4b659a835cf2b859e9b9
Source dataset
uspto-grants-2013_10
Patent number
US08551981B2

Reaction notes

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