Dimethylformamide → Benzoyl cytosin-1-ylacetate

HRID 1170032Notes

Reaction equation

[NH:1]1[CH:8]=[CH:7][C:5]([NH2:6])=[N:4][C:2]1=[O:3].[H-].[Na+].Br[CH2:12][C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14].CN(C=[O:27])C>>[N:1]1([CH2:12][C:13]([O:15][C:16](=[O:27])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])[CH:8]=[CH:7][C:5]([NH2:6])=[N:4][C:2]1=[O:3]

Participants

Reactant 4

HCID 6228Dimethylformamide

HCID 24758Sodium hydride

HCID 62576Benzyl bromoacetate

HCID 178418229Cytosine

Product 1

HCID 53946337Benzoyl cytosin-1-ylacetate

Conditions

Temperature: 50 °C

Procedure

Reference is made to FIG. 1 where to cytosine (20 g, 0.18 mmol) in 400 mL DMF was added 7.2 g (0.18 mmol) of NaH (disp. in oil 60%). The mixture was heated to 50° C. and stirred for 2 h under nitrogen. After cooling to room temperature, 29 mL (1.1 eq.) of benzyl bromoacetate was added over 2 h. After stirring overnight, the dark suspension was filtered and the filtrate washed with cold DMF and 0.2 M sodium bicarbonate. The product (1) was crystallized from ethanol. Yield: 37 g (79%). 1H NMR (d6-DMSO): δ 4.56 (s, 2 CH2O), 5.24 (s, 2 H, CH2CO), 5.77 (d, 1 H, H5), 7.20 (dd, 2 H, NH2), 7.45 (m, 5 H, aromatic), 7.65 (d, 1 H, H6). MS (FAB) m/z 260 (M+H)+ (calcd 260).

Workup

temperatureAfter cooling to room temperature
stirringAfter stirring overnight
filtrationthe dark suspension was filtered
washthe filtrate washed with cold DMF and 0.2 M sodium bicarbonate
customThe product (1) was crystallized from ethanol

Sources & evidence

ORD record: ord-b3fa69c36ba7456fb863a27113170396
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07825215B1

Reaction notes

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