Water → HCID 86726108, compound

HRID 2169482Notes

Reaction equation

HRID 2169482 reaction equation
[CH:1]1([N:4]([CH2:34][CH2:35]O)[C:5]([C:7]2[C:12]([O:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[C:11]([OH:21])[N:10]=[C:9]([CH2:22][C:23]3([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=4)[CH2:27][CH2:26][CH2:25][CH2:24]3)[N:8]=2)=[O:6])[CH2:3][CH2:2]1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.C(OCC)(=O)C.O>ClCCl>[CH2:14]([O:13][C:12]1[C:11](=[O:21])[N:10]=[C:9]([CH2:22][C:23]2([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=3)[CH2:27][CH2:26][CH2:25][CH2:24]2)[N:8]2[CH2:35][CH2:34][N:4]([CH:1]3[CH2:3][CH2:2]3)[C:5](=[O:6])[C:7]=12)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 178519974HCID 178519974, compound

Product 1

HCID 86726108HCID 86726108, compoundYield 349.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 5-benzyloxy-6-hydroxy-2-(1-pyridin-2-yl-cyclopentylmethyl)-pyrimidine-4-carboxylicacidcyclopropyl-(2-hydroxyethyl)-amide (451) (80 mg, 0.164 mmol), in dichloromethane (6 mL), TPP (150.33 mg, 0.574 mmol) and diisopropyl azodicarboxylate (0.097 mL, 0.492 mmol) were added and stirring was continued for 1 h at room temperature while silica thin layer chromatography was performed (100% ethyl acetate, Rf=0.2). After completion of the reaction, water (5 mL) was added and the mixture was extracted with dichloromethane (2×25 mL). The combined extracts were dried and concentrated to get crude 9-benzyloxy-2-cyclopropyl-6-(1-pyridin-2-yl-cyclopentylmethyl)-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione (452) (270 mg, Crude) as a yellow gummy liquid.

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with dichloromethane (2×25 mL)
  3. customThe combined extracts were dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-9afbff29098842aa955e766d9554d6ae
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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