N-[2-Amino-4-chloro-6-[[(1R,4S)-4-(hydroxymethyl)-2-cyclopenten-1-yl]amino]-5-pyrimidinyl]formamide

Base Information

• Chemical Name: N-[2-Amino-4-chloro-6-[[(1R,4S)-4-(hydroxymethyl)-2-cyclopenten-1-yl]amino]-5-pyrimidinyl]formamide
• CAS No.: 171887-04-0
• Molecular Formula: C11H14 Cl N5 O2
• Molecular Weight: 283.717
• Mol file: 171887-04-0.mol

Synonyms:Formamide,N-[2-amino-4-chloro-6-[[4-(hydroxymethyl)-2-cyclopenten-1-yl]amino]-5-pyrimidinyl]-,(1R-cis)-;N-[2-Amino-4-chloro-6-[[(1R,4S)-4-(hydroxymethyl)-2-cyclopenten-1-yl]amino]-5-pyrimidinyl]formamide;

Chemical Property of N-[2-Amino-4-chloro-6-[[(1R,4S)-4-(hydroxymethyl)-2-cyclopenten-1-yl]amino]-5-pyrimidinyl]formamide

Chemical Property:

• Appearance/Colour: white-off powder or granule
• Boiling Point: 675.0±65.0 °C(Predicted)
• PKA: 11.47±0.70(Predicted)
• PSA: 113.16000
• Density: 1.550
• LogP: 1.99250
• Storage Temp.: 2-8°C

Purity/Quality:

98%,99%, ^*data from raw suppliers

(1R-cis)-N-[2-amino-4-chloro-6-[[4-(hydroxymethyl)-2-cyclopenten-1-yl]amino]-5-pyrimidinyl]-formamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: (1R-cis)-N-[2-amino-4-chloro-6-[[4-(hydroxymethyl)-2-cyclopenten-1-yl]amino]-5-pyrimidinyl]-formamide is an intermediate used in the synthesis of the HIV reverse transcriptase inhibitor ziagen.

Technology Process of N-[2-Amino-4-chloro-6-[[(1R,4S)-4-(hydroxymethyl)-2-cyclopenten-1-yl]amino]-5-pyrimidinyl]formamide

There total 7 articles about N-[2-Amino-4-chloro-6-[[(1R,4S)-4-(hydroxymethyl)-2-cyclopenten-1-yl]amino]-5-pyrimidinyl]formamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 88.2%

((1S,4R)-4-aminocyclopent-2-enyl)methanol D-hydrogen tartrate (229177-52-0) + N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide (171887-03-9) → (1R,4S)-1-[(2-amino-6-chloro-5-formamido-4-pyrimidinyl)amino]-4-(hydroxymethyl)-2-cyclopentene (171887-04-0)

Guidance literature:

((1S,4R)-4-aminocyclopent-2-enyl)methanol D-hydrogen tartrate; With sodium carbonate; In isopropyl alcohol; at 20 ℃; for 1h;

N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide; In isopropyl alcohol; Concentration; Solvent; Reflux;

Reference yield: 85.0%

(1R,4S)-1-amino-4-hydroxymethyl-2-cyclopentene (136522-35-5) + N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide (171887-03-9) → (1R,4S)-1-[(2-amino-6-chloro-5-formamido-4-pyrimidinyl)amino]-4-(hydroxymethyl)-2-cyclopentene (171887-04-0)

Guidance literature:

With triethylamine; In ethanol; water;

Reference yield: 74.0%

(1R,4S)-1-amino-4-(hydroxymethyl)-2-cyclopentene hydrochloride (168960-19-8,287717-44-6) + N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide (171887-03-9) → (1R,4S)-1-[(2-amino-6-chloro-5-formamido-4-pyrimidinyl)amino]-4-(hydroxymethyl)-2-cyclopentene (171887-04-0)

Guidance literature:

With sodium hydroxide; triethylamine; In 2-methyl-propan-1-ol;

upstream raw materials:

(1R,4S)-1-amino-4-hydroxymethyl-2-cyclopentene

N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide

(-)-2-azabicyclo[2.2.1]hept-5-en-3-one

2-amino-5-{[(dimethylamino)methylene]amino}-4,6-dichloropyrimidine

Downstream raw materials:

(1S, 4R)-(4-(2,5-diamino-6-chloro-4-pyrimidinyl)amino)-2-cyclopenten-1-methanol

abacavir

((1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)cyclopent-2-en-1-yl)methanol hydrochloride

Refernces

• 1、 -. "PROCESS FOR THE PREPARATION OF AMINO ALCOHOL DERIVATIVES OR SALTS THEREOF". Paragraph 0050; 0051. . Retrieved 2017/09/02.
• 2、 -. "Enantiomer compositions of (1R,4S)-1-butyrylamino-4-(hydroxymethyl)-2-cyclopentene". . . Retrieved 2008/06/13.