9-benzyloxy-2-cyclopropyl-6-(1-phenyl-cyclopentylmethyl)-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione → 9-Benzyloxy-2-oxetan-3-yl-6-(1-phenyl-cyclopentylmethyl)-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione

HRID 2169333Notes

Reaction equation

HRID 2169333 reaction equation
C(OC1C(=O)N=C(CC2(C3C=CC=CC=3)CCCC2)N2CCN(C3CC3)C(=O)C=12)C1C=CC=CC=1.O[CH2:37][CH2:38][N:39]([CH:69]1[CH2:72][O:71][CH2:70]1)[C:40]([C:42]1[C:47]([O:48][CH2:49][C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)=[C:46]([OH:56])[N:45]=[C:44]([CH2:57][C:58]2([C:63]3[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=3)[CH2:62][CH2:61][CH2:60][CH2:59]2)[N:43]=1)=[O:41]>>[CH2:49]([O:48][C:47]1[C:46](=[O:56])[N:45]=[C:44]([CH2:57][C:58]2([C:63]3[CH:64]=[CH:65][CH:66]=[CH:67][CH:68]=3)[CH2:59][CH2:60][CH2:61][CH2:62]2)[N:43]2[CH2:37][CH2:38][N:39]([CH:69]3[CH2:70][O:71][CH2:72]3)[C:40](=[O:41])[C:42]=12)[C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1

Participants

3

Reactant 2

HCID 867259579-benzyloxy-2-cyclopropyl-6-(1-phenyl-cyclopentylmethyl)-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dioneHCID 178519966HCID 178519966, compound

Product 1

HCID 867259729-Benzyloxy-2-oxetan-3-yl-6-(1-phenyl-cyclopentylmethyl)-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dioneYield 80.9%

Procedure

This compound was prepared following the same method as described for 9-benzyloxy-2-cyclopropyl-6-(1-phenyl-cyclopentylmethyl)-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione (286) from 5-benzyloxy-6-hydroxy-2-(1-phenyl-cyclopentylmethyl)-pyrimidine-4-carboxylic acid (2-hydroxyethyl)-oxetan-3-yl-amide (297) (150 mg, 0.28 mmol). The product was obtained as off-white solid (110 mg, 80.65%).

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-fcabbe47d84b4f50ada1479c9c74485c
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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