Sulfuric Acid → 2,4-Diamino-6-ethyl-5-(3-(2-(2-ethoxycarbonylethyl)phenoxy)propoxy)pyrimidine

HRID 40822Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([O:9][CH2:10][CH2:11][CH2:12][O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH2:20][CH2:21][C:22]([OH:24])=[O:23])=[C:4]([CH2:25][CH3:26])[N:3]=1.OS(O)(=O)=O.C(OCC)(OCC)O[CH2:34][CH3:35].C([O-])([O-])=O.[K+].[K+]>CCO>[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([O:9][CH2:10][CH2:11][CH2:12][O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH2:20][CH2:21][C:22]([O:24][CH2:34][CH3:35])=[O:23])=[C:4]([CH2:25][CH3:26])[N:3]=1

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of 2,4-diamino-6-ethyl-5-(3-(2-(2-carboxyethyl)phenoxy)propoxy)pyrimidine (0.3604 g, 1 mmol) and a catalytic amount of con. H2SO4 in EtOH (4 mL) was added triethyl orthoformate (2 mL) and the mixture was left stirring at 25° C. for 8 hours. The reaction mixture was neutralized with K2CO3 and evaporated to dryness. The crude product was diluted with water and extracted with CH2Cl2. Evaporation to dryness gave the desired ester as white solid (0.3496 g, 90%, mp. 124.5-1255.5° C.). 1H NMR (500 MHz, DMSO-d6): 1.24 (3H, t, J=7.3 Hz), 1.26 (3H, t, J=7.7 Hz), 2.26 (2H, m), 2.59 (2H, q, J=7.7 Hz), 2.62 (2H, t, J=7.7 Hz), 2.95 (2H, t, J=7.7 Hz), 3.98 (2H, t, J=6.0 Hz), 4.13 (2H, q, J=7.1 Hz), 4.27 (2H, t, J=5.7 Hz), 5.17 (2H, bs), 5.28 (2H, bs), 6.90 (1H, d, J=8.2 Hz), 6.93 (1H, t, J=7.5 Hz), 7.17 (1H, dd, J=7.4, 1.4 Hz), 7.22 (1H, dt, J=7.8, 1.5 Hz).

Workup

waitthe mixture was left
customevaporated to dryness
additionThe crude product was diluted with water
extractionextracted with CH2Cl2
customEvaporation to dryness

Sources & evidence

ORD record: ord-d69ac2f2b9804a5da5a607281ca1cf14
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08530491B2

Reaction notes

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