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

HRID 2169454Notes

Reaction equation

HRID 2169454 reaction equation
C(OC1C(=O)N=C(CC2(N3C4=NC=CC=C4C=C3)CCCC2)N2CCN(C)C(=O)C=12)C1C=CC=CC=1.O[CH2:38][CH2:39][N:40]([CH:73]1[CH2:76][O:75][CH2:74]1)[C:41]([C:43]1[C:48]([O:49][CH2:50][C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)=[C:47]([OH:57])[N:46]=[C:45]([CH2:58][C:59]2([N:64]3[C:68]4=[N:69][CH:70]=[CH:71][CH:72]=[C:67]4[CH:66]=[CH:65]3)[CH2:63][CH2:62][CH2:61][CH2:60]2)[N:44]=1)=[O:42]>>[CH2:50]([O:49][C:48]1[C:47](=[O:57])[N:46]=[C:45]([CH2:58][C:59]2([N:64]3[C:68]4=[N:69][CH:70]=[CH:71][CH:72]=[C:67]4[CH:66]=[CH:65]3)[CH2:60][CH2:61][CH2:62][CH2:63]2)[N:44]2[CH2:38][CH2:39][N:40]([CH:73]3[CH2:76][O:75][CH2:74]3)[C:41](=[O:42])[C:43]=12)[C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1

Participants

3

Reactant 2

HCID 867260709-benzyloxy-2-methyl-6-(1-pyrrolo[2,3-b]pyridin-1-yl-cyclopentylmethyl)-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dioneHCID 178519979HCID 178519979, compound

Product 1

HCID 867260859-Benzyloxy-2-oxetan-3-yl-6-(1-pyrrolo[2,3-b]pyridin-1-yl-cyclopentylmethyl)-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione

Procedure

9-Benzyloxy-2-oxetan-3-yl-6-(1-pyrrolo[2,3-b]pyridin-1-yl-cyclopentylmethyl)-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione (423) was prepared following the same method as described for 9-benzyloxy-2-methyl-6-(1-pyrrolo[2,3-b]pyridin-1-yl-cyclopentylmethyl)-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione (407) from 5-benzyloxy-6-hydroxy-2-(1-pyrrolo[2,3-b]pyridin-1-yl-cyclopentylmethyl)-pyrimidine-4-carboxylic acid (2-hydroxyethyl)-oxetan-3-yl-amide (422) (200 mg, 0.40 mmol) and was obtained as white sticky solid (13 mg, 6%).

Sources & evidence

ORD record
ord-cb9ffdd66406410cab741bd992987030
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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