Water → (R)-2-(2-chloro-6,7-dihydro-thieno[3,2-d]pyrimidin-4-ylamino)-3-methyl-butyramide

HRID 70086Notes

Reaction equation

HRID 70086 reaction equation
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[S:10][CH2:9][CH2:8][C:6]=2[N:7]=1.Cl.[NH2:13][C@@H:14]([C:18]([NH2:20])=[O:19])[CH:15]([CH3:17])[CH3:16].C(N(C(C)C)CC)(C)C.O>O1CCOCC1>[Cl:1][C:2]1[N:3]=[C:4]([NH:13][C@H:14]([CH:15]([CH3:17])[CH3:16])[C:18]([NH2:20])=[O:19])[C:5]2[S:10][CH2:9][CH2:8][C:6]=2[N:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 457899672,4-Dichloro-6,7-dihydrothieno[3,2-d]pyrimidineHCID 53486046(2R)-2-amino-3-methylbutanamide hydrochloride

Product 1

HCID 59708380(R)-2-(2-chloro-6,7-dihydro-thieno[3,2-d]pyrimidin-4-ylamino)-3-methyl-butyramideYield 74%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

800 mg 2,4-dichloro-6,7-dihydro-thieno[3,2-d]pyrimidine and 800 mg D-valinamide hydrochloride are placed in 8 ml dioxane, then 2.7 ml diisopropylethylamine are added. The reaction mixture is heated to 120° C. in the microwave for 2 hours. The residue is mixed with water. The precipitate formed is suction filtered and dried. 820 mg of the product are obtained as a powder Analytical HPLC (method R): RT=2.64 min.

Workup

  1. customThe precipitate formed
  2. filtrationfiltered
  3. customdried

Sources & evidence

ORD record
ord-71d8978c174343739491a48a4e6cd835
Source dataset
uspto-grants-2014_09
Patent number
US08822474B2

Reaction notes

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