Diisopropylethylamine → (R)-2-(2-chloro-6,7-dihydrothieno[3,2-d]pyrimidin-4-ylamino)-pentan-1-ol

HRID 1751786Notes

Reaction equation

HRID 1751786 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.C(N(C(C)C)CC)(C)C.[NH2:21][C@@H:22]([CH2:26][OH:27])[CH2:23][CH2:24][CH3:25]>O1CCOCC1>[Cl:1][C:2]1[N:3]=[C:4]([NH:21][C@H:22]([CH2:23][CH2:24][CH3:25])[CH2:26][OH:27])[C:5]2[S:10][CH2:9][CH2:8][C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 5324727(2R)-2-aminopentan-1-olHCID 457899672,4-Dichloro-6,7-dihydrothieno[3,2-d]pyrimidine

Product 1

HCID 59708491(R)-2-(2-chloro-6,7-dihydrothieno[3,2-d]pyrimidin-4-ylamino)-pentan-1-ol

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

1.4 g 2,4-dichloro-6,7-dihydrothieno[3,2-d]pyrimidine (II) are placed in 9 ml dioxane, then 3.5 ml diisopropylethylamine are added followed by 0.9 g D-norvalinol. The reaction mixture is heated in the microwave at 120° C. until there is no further reaction then cooled and evaporated down. The residue is treated with petroleum ether/ethyl acetate 9:1 in the ultrasound bath, the solid is suction filtered and dried. 1.5 g (III-3) are obtained in the form of a solid. 1H NMR (400 MHz, DMSO): 4.67 (1H, t); 0.86 (3H, t).

Workup

  1. customno further reaction
  2. temperaturethen cooled
  3. customevaporated down
  4. additionThe residue is treated with petroleum ether/ethyl acetate 9:1 in the ultrasound bath
  5. filtrationfiltered
  6. customdried
  7. custom1.5 g (III-3) are obtained in the form of a solid

Sources & evidence

ORD record
ord-23c820a1a13046239bbda40aafca30d0
Source dataset
uspto-grants-2015_10
Patent number
US09161927B2

Reaction notes

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