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

HRID 2169402Notes

Reaction equation

HRID 2169402 reaction equation
C(OC1C(=O)N=C(CC2(C3C4C(=CC=CC=4)C=CC=3)CCCC2)N2CCN(C3CC3)C(=O)C=12)C1C=CC=CC=1.O[CH2:41][CH2:42][N:43]([CH:77]1[CH2:82][CH2:81][O:80][CH2:79][CH2:78]1)[C:44]([C:46]1[C:51]([O:52][CH2:53][C:54]2[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=2)=[C:50]([OH:60])[N:49]=[C:48]([CH2:61][C:62]2([C:67]3[C:76]4[C:71](=[CH:72][CH:73]=[CH:74][CH:75]=4)[CH:70]=[CH:69][CH:68]=3)[CH2:66][CH2:65][CH2:64][CH2:63]2)[N:47]=1)=[O:45]>>[CH2:53]([O:52][C:51]1[C:50](=[O:60])[N:49]=[C:48]([CH2:61][C:62]2([C:67]3[C:76]4[C:71](=[CH:72][CH:73]=[CH:74][CH:75]=4)[CH:70]=[CH:69][CH:68]=3)[CH2:66][CH2:65][CH2:64][CH2:63]2)[N:47]2[CH2:41][CH2:42][N:43]([CH:77]3[CH2:78][CH2:79][O:80][CH2:81][CH2:82]3)[C:44](=[O:45])[C:46]=12)[C:54]1[CH:55]=[CH:56][CH:57]=[CH:58][CH:59]=1

Participants

3

Reactant 2

HCID 867260219-benzyloxy-2-cyclopropyl-6-(1-naphthalen-1-yl-cyclopentylmethyl)-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dioneHCID 178519958HCID 178519958, compound

Product 1

HCID 867260339-Benzyloxy-6-(1-naphthalen-1-yl-cyclopentylmethyl)-2-(tetrahydro-pyran-4-yl)-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione

Procedure

This compound was prepared following the same method as described for pure 9-benzyloxy-2-cyclopropyl-6-(1-naphthalen-1-yl-cyclopentylmethyl)-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione (356) from 5-benzyloxy-6-hydroxy-2-(1-naphthalen-1-yl-cyclopentylmethyl)-pyrimidine-4-carboxylic acid (2-hydroxyethyl)-(tetrahydro-pyran-4-yl)-amide (367) (110 mg, 0.2 mmol). Purification was done on silica gel (normal, 100-200 mesh) using 1% to 5% methanol in dichloromethane as gradient eluent. The yield was 96 mg, 90%, of a white solid.

Workup

  1. customThis compound was prepared
  2. customPurification

Sources & evidence

ORD record
ord-b6c5e8e24a5b41f3b17b37d15656a515
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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