3-Amino-1-propanol → 3-(2-Chloro-5-iodopyrimidine-4-ylamino)propan-1-ol

HRID 1169733Notes

Reaction equation

HRID 1169733 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][OH:5].C(N(C(C)C)C(C)C)C.[Cl:15][C:16]1[N:21]=[C:20](Cl)[C:19]([I:23])=[CH:18][N:17]=1>C(#N)C>[Cl:15][C:16]1[N:21]=[C:20]([NH:1][CH2:2][CH2:3][CH2:4][OH:5])[C:19]([I:23])=[CH:18][N:17]=1

Participants

5

Reactant 3

HCID 90863-Amino-1-propanolHCID 81531DiisopropylethylamineHCID 2634382,4-Dichloro-5-iodopyrimidine

Product 1

HCID 595508483-(2-Chloro-5-iodopyrimidine-4-ylamino)propan-1-ol

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
-40 °C

Procedure

In accordance with procedure 2, 3-amino-1-propanol (0.38 ml, 5 mmol) and N-ethyldiisopropylamine (1.74 ml, 10 mmol) are dissolved in 100 ml acetonitrile under argon and cooled to −40° C. Next, the solution of 2,4-dichloro-5-iodo-pyrimidine (1.51, 5.5 mmol) in 50 ml acetonitrile is added dropwise at −40° C. internal temperature. The mixture is then stirred for 1 hr at −40° C., for a further 5 hrs at −37 to −25° C., slowly warmed to RT and stirred for 18 hrs at RT.

Workup

  1. temperatureslowly warmed to RT
  2. stirringstirred for 18 hrs at RT

Sources & evidence

ORD record
ord-2b0149a7199a4233985d2bdd71add3d7
Source dataset
uspto-grants-2010_11
Patent number
US07825128B2

Reaction notes

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