Sodium Hydroxide → HCID 135578124, compound

HRID 2165724Notes

Reaction equation

C([NH:4][C:5]1[NH:6][C:7](=[O:33])[C:8]([CH2:18][CH2:19][CH2:20][NH:21][C:22]2[CH:32]=[CH:31][C:25]([C:26]([O:28]CC)=[O:27])=[CH:24][CH:23]=2)=[C:9]([N:11](C(=O)C)C(=O)C)[N:10]=1)(=O)C.[OH-].[Na+]>C(O)C>[NH2:4][C:5]1[NH:6][C:7](=[O:33])[C:8]([CH2:18][CH2:19][CH2:20][NH:21][C:22]2[CH:32]=[CH:31][C:25]([C:26]([OH:28])=[O:27])=[CH:24][CH:23]=2)=[C:9]([NH2:11])[N:10]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of 0.22 g (0.47 mmol) of ethyl 4-[3-[2-(acetylamino)-4-(diacetylamino)-1,6-dihydro-6-oxo-5-pyrimidinyl]propylamino]benzoate in 7.0 ml of 95% ethyl alcohol was added 15 ml of 1.0N NaOH. The reaction was heated at 70° C. for 20 hours. The mixture was reduced by spin evaporation in vacuo to a 10-ml volume and adjusted to pH 5 with 1.0N HCl. The precipitate was collected by filtration, washed with water, and dried in vacuo to yield 0.11 g (71% of theory) of 4-[3-(2,4-diamino-1,6-dihydro-6-oxo-5-pyrimidinyl)propylamino]benzoic acid one-half sodium salt as a white solid, mp 273° (dec.); HPLC on Versapack C-18 (10 micron; 4.6×250 mm) with aqueous 60% methanol containing 0.2% trifluoroacetic acid gave one major peak, k1 =0.58; NMR (DMSO-d6) δ 1.58 (m, 2H, CCH2C), 2.24 (t, 2H, Het--CH2), 3.02 (m, 2H, CH2N), 5.77 (br s, 2H, NH2), 5.94 (br s, 2H, NH2), 6.46 (t, 1H, NH--Ar), 6.54 (d, 2H, Ar), 7.65 (d, 2H, Ar), 9.80 (br s, 1H, NH), 11.95 (br s, 0.5 H, CO2H). Elemental analysis. Calculated for C14H16N5O3Na0.5.0.75 H2O (MW 327.82); C, 51.29; H, 5.53; N, 21.36; Na, 3.51. Found: C, 51.34; H, 5.39; N, 21.32; Na, 3.33.

Workup

customThe mixture was reduced by spin evaporation in vacuo to a 10-ml volume
filtrationThe precipitate was collected by filtration
washwashed with water
customdried in vacuo

Sources & evidence

ORD record: ord-b64ca4d300b74bc19d54089166864020
Source dataset: uspto-grants-1990_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04940713

Reaction notes

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