Water → Ethyl 2-[5-(naphthalene-2-carbonyl)hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl]pyrimidine-5-carboxylate

HRID 2079816Notes

Reaction equation

HRID 2079816 reaction equation
[CH2:1]1[CH:5]2[CH2:6][NH:7][CH2:8][CH:4]2[CH2:3][N:2]1[C:9]1[N:14]=[CH:13][C:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:11][N:10]=1.[CH:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[CH:22][C:21]=1[C:30](Cl)=[O:31].O>N1C=CC=CC=1>[CH:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[CH:22][C:21]=1[C:30]([N:7]1[CH2:6][CH:5]2[CH2:1][N:2]([C:9]3[N:14]=[CH:13][C:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:11][N:10]=3)[CH2:3][CH:4]2[CH2:8]1)=[O:31]

Participants

5

Reactant 3

HCID 962WaterHCID 752462-Naphthoyl chlorideHCID 59367682Ethyl 2-hexahydropyrrolo[3,4-c]pyrrol-2(1H)-ylpyrimidine-5-carboxylate

Product 1

HCID 59367685Ethyl 2-[5-(naphthalene-2-carbonyl)hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl]pyrimidine-5-carboxylateYield 88.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a suspension of ethyl 2-hexahydropyrrolo[3,4-c]pyrrol-2(1H)-ylpyrimidine-5-carboxylate (0.156 g, 0.59 mmol) in pyridine (2 ml) was added 2-naphthalene carbonyl chloride (0.136 g, 0.71 mmol). The mixture was stirred for 3 h, then water (10 ml) was added and the product collected by filtration. The product was washed with further water and then dried overnight under vacuum to yield the title compound (0.217 g, 71%).

Workup

  1. filtrationthe product collected by filtration
  2. washThe product was washed with further water
  3. customdried overnight under vacuum

Sources & evidence

ORD record
ord-59d0c307ca9f413292a14d257699c13b
Source dataset
uspto-grants-2011_04
Patent number
US07932246B2

Reaction notes

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