HCID 19789719, compound → HCID 19789735, compound

HRID 1655934Notes

Reaction equation

HRID 1655934 reaction equation
[Cl:1][C:2]1[C:7]([NH:8][CH:9]=O)=[C:6]([NH:11][O:12][CH2:13][CH2:14][CH2:15][O:16][CH2:17][O:18][CH:19]([CH3:21])[CH3:20])[N:5]=[C:4]([NH:22][CH:23]=[O:24])[N:3]=1>C(OC(OCC)OCC)(=O)C>[Cl:1][C:2]1[N:3]=[C:4]([NH:22][CH:23]=[O:24])[N:5]=[C:6]2[C:7]=1[N:8]=[CH:9][N:11]2[O:12][CH2:13][CH2:14][CH2:15][O:16][CH2:17][O:18][CH:19]([CH3:21])[CH3:20]

Participants

3

Reactant 1

HCID 19789719HCID 19789719, compound

Product 1

HCID 19789735HCID 19789735, compoundYield 60.3%

Reagents, catalysts & solvents 1

HCID 84166Methanol, 1,1-diethoxy-, 1-acetateSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 4-chloro-2,5-diformamido-6-[3-(isopropoxymethoxy)propoxyamino]pyrimidine (3.3 g, 9.12 mmol) and diethoxymethyl acetate (10 ml) was heated at 120° C. for 1 hr. The solution was then evaporated and the residue taken up into methanol (30 ml) and concentrated aqueous ammonia (3 ml). After 1 hr. at 20° C. the solvent was removed and the residue purified by column chromatography on silica gel eluting with hexane:ethyl acetate (1:1) to afford 6-chloro-2-formamido-9-[3-(isopropoxymethoxy)propoxy]purine (1.89 g; 60%), νmax (KBr) 2970, 1697, 1609, 1581, 1503, 1383 cm-1 ; δH [(CD3)2SO], 1.10 (6H, d, J=6.3 Hz, 2×CH3), 1.97 (2H, quintet, J=6.3 Hz, CH2CH2CH2), 3.67 (2H, t, J=6.3 Hz, CH2OC), 3.77 (1H, septet, J=6.3 Hz, CH), 4.49 (2H, t, J=6.3 Hz, CH2ON), 4.65 (2H, s, OCH2O), 8.81 (1H, s, H-8), 9.37 (1H, d, J=9.1 Hz, CHO), 11.30 (1H, br.s, J=9.1 Hz, NH).

Workup

  1. customThe solution was then evaporated
  2. customat 20° C. the solvent was removed
  3. customthe residue purified by column chromatography on silica gel eluting with hexane:ethyl acetate (1:1)

Sources & evidence

ORD record
ord-28c17189015140f18e57650bfa121da0
Source dataset
uspto-grants-1993_10
Patent number
US05252575

Reaction notes

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