Trimethyl orthoformate → HCID 58654417, compound

HRID 1170539Notes

Reaction equation

HRID 1170539 reaction equation
[BH3-]C#N.[Na+].[N:5]1([C:10]2[N:15]=[C:14]([CH:16]3[CH:20]([C:21]([NH:23][CH3:24])=[O:22])[CH2:19][CH2:18][NH:17]3)[CH:13]=[C:12]([CH3:25])[N:11]=2)[CH:9]=[CH:8][N:7]=[CH:6]1.[O:26]1[C:30]2[CH:31]=[CH:32][C:33]([CH2:35][N:36]([CH2:44][CH:45]=O)[C:37](=[O:43])[O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[CH:34][C:29]=2[O:28][CH2:27]1.C(OC)(OC)OC>C(O)(=O)C.O>[N:5]1([C:10]2[N:15]=[C:14]([CH:16]3[CH:20]([C:21](=[O:22])[NH:23][CH3:24])[CH2:19][CH2:18][N:17]3[CH2:45][CH2:44][N:36]([CH2:35][C:33]3[CH:32]=[CH:31][C:30]4[O:26][CH2:27][O:28][C:29]=4[CH:34]=3)[C:37](=[O:43])[O:38][C:39]([CH3:41])([CH3:40])[CH3:42])[CH:13]=[C:12]([CH3:25])[N:11]=2)[CH:9]=[CH:8][N:7]=[CH:6]1

Participants

7

Reactant 4

HCID 9005Trimethyl orthoformateHCID 5003444Sodium cyanoborohydrideHCID 57355452tert-Butyl [(2H-1,3-benzodioxol-5-yl)methyl](2-oxoethyl)carbamateHCID 58654424HCID 58654424, compound

Product 1

HCID 58654417HCID 58654417, compoundYield 22.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 962WaterSolvent

Procedure

NaBH3CN (76 mg, 1.2 mmol) was added all at once to a stirred solution of 2-(2-(1H-imidazol-1-yl)-6-methylpyrimidin-4-yl)-N-methylpyrrolidine-3-carboxamide (230 mg, 0.80 mmol), tert-butyl benzo[d][1,3]dioxol-5-ylmethyl(2-oxoethyl)carbamate (280 mg, 0.95 mmol), acetic acid (100 μL, 1.59 μmol) and trimethyl orthoformate (20 ml). The reaction mixture stirred at rt for 16 h then water (20 mL) was added. The solution was extracted with EtOAc (2×20 mL), the combined organic layers were dried over Na2SO4, filtered and concentrated under vacuum. The residue was purified using column chromatography (20:1 CHCl3/MeOH) to afford 100 mg (22%) of tert-butyl 2-(2-(2-(1H-imidazol-1-yl)-6-methylpyrimidin-4-yl)-3-(methylcarbamoyl)pyrrolidin-1-yl)ethyl(benzo[d][1,3]dioxol-5-ylmethyl)carbamate as a colorless oil.

Workup

  1. extractionThe solution was extracted with EtOAc (2×20 mL)
  2. dry with materialthe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum
  5. customThe residue was purified

Sources & evidence

ORD record
ord-e1289ad9975f469ca52d692c6730a514
Source dataset
uspto-grants-2010_11
Patent number
US07825256B2

Reaction notes

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