Triethylamine → (R)-2-(2-Chloro-5-iodo-pyrimidin-4-ylamino)-3-methyl-butan-1-ol

HRID 272632

Reaction equation

HRID 272632 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([I:9])=[CH:4][N:3]=1.C(N(CC)CC)C.[NH2:17][C@H:18]([CH:21]([CH3:23])[CH3:22])[CH2:19][OH:20]>C(#N)C.O>[Cl:1][C:2]1[N:7]=[C:6]([NH:17][C@H:18]([CH:21]([CH3:23])[CH3:22])[CH2:19][OH:20])[C:5]([I:9])=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 2634382,4-Dichloro-5-iodopyrimidineHCID 6950587D-Valinol

Product 1

HCID 59674020(R)-2-(2-Chloro-5-iodo-pyrimidin-4-ylamino)-3-methyl-butan-1-ol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of 10.05 g (36.6 mmol) of 2,4-Dichloro-5-iodo-pyrimidine and 5.6 ml (40.0 mmol) triethylamine in 30 ml of acetonitrile is mixed with 4.85 g (47.0 mmol) of (R)-2-Amino-3-methyl-butan-1-ol. The batch is stirred at room temperature for 16 hours and is finally diluted with water. The batch is filtered and the solid is washed with small amounts of acetonitrile and water. The solid is dried. 10.24 g (30.0 mmol, corresponding to 82% of theory) of the product is obtained.

Workup

  1. filtrationThe batch is filtered
  2. washthe solid is washed with small amounts of acetonitrile and water
  3. customThe solid is dried
  4. custom10.24 g (30.0 mmol, corresponding to 82% of theory) of the product is obtained

Sources & evidence

ORD record
ord-840b4cd1819e43acb5e41b8f14a7d16d
Source dataset
uspto-grants-2008_11
Patent number
US07456191B2

Linked notes

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