Triethylamine → HCID 9795791, compound

HRID 369504Notes

Reaction equation

HRID 369504 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([NH:9][CH:10]=[O:11])=[C:4](Cl)[N:3]=1.Cl.[NH2:14][C@@H:15]1[CH2:19][C@H:18]([CH2:20][OH:21])[CH:17]=[CH:16]1.C(N(CC)CC)C.[OH-].[Na+]>C(O)C(C)C>[NH2:1][C:2]1[N:3]=[C:4]([NH:14][C@@H:15]2[CH2:19][C@H:18]([CH2:20][OH:21])[CH:17]=[CH:16]2)[C:5]([NH:9][CH:10]=[O:11])=[C:6]([Cl:8])[N:7]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 10198177N-(2-Amino-4,6-dichloropyrimidin-5-yl)formamideHCID 53471860[(1S,4R)-4-Amino-2-cyclopenten-1-yl]methanol hydrochloride (1:1)

Product 1

HCID 9795791HCID 9795791, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6560IsobutanolSolvent2×

Conditions

Temperature
80 °C

Procedure

2.07 g of N-(2-amino-4,6-dichloro-5-pyrimidinyl)formamide were heated to 80° C. in 40 ml of isobutanol (white suspension). A solution of 1.97 g of (1R,4S)-1-amino-4-hydroxymethyl-2-cyclopentene hydrochloride, 3.8 g of triethylamine and 15 ml of isobutanol was added to the mixture. The mixture was stirred at 80° C. for a further 13 h. 10 ml of 1N NaOH were added to the clear solution at 20° C., followed by evaporation to dryness. The residue underwent flash chromatography (silica gel 60 column, length 8 cm, diameter 6.5 cm, eluent ethyl acetate/methanol 95/5). After evaporating off the eluent and drying the residue, 2.1 g of title compound were obtained. The yield was 74%.

Workup

  1. customfollowed by evaporation to dryness
  2. customAfter evaporating off the eluent
  3. customdrying the residue

Sources & evidence

ORD record
ord-036df17b63e549ac87a96b68441e306d
Source dataset
uspto-grants-2000_10
Patent number
US06137007

Reaction notes

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