Diisopropylethylamine → HCID 59708434, compound

HRID 518014Notes

Reaction equation

HRID 518014 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]([CH:25]([CH3:27])[CH3:26])[CH2:23][OH:24]>O1CCOCC1>[Cl:1][C:2]1[N:3]=[C:4]([NH:21][C@H:22]([CH:25]([CH3:27])[CH3:26])[CH2:23][OH:24])[C:5]2[S:10][CH2:9][CH2:8][C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 6950587D-ValinolHCID 457899672,4-Dichloro-6,7-dihydrothieno[3,2-d]pyrimidine

Product 1

HCID 59708434HCID 59708434, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

7.2 g 2,4-dichloro-6,7-dihydro-thieno[3,2-d]pyrimidin (II) are placed in 36 ml dioxane, then 18 ml diisopropylethylamine and then 6.1 g (R)-(−)-2-amino-3-methyl-1-butanol are added. The reaction mixture is heated to 100° C. until no further reaction takes place, then cooled and evaporated down. The residue is treated with petroleum ether/ethyl acetate 9:1 in the ultrasound bath and the solid is suction filtered and dried. 8.3 g (III-2) are obtained as a solid. Analytical HPLC (method A): RT=2.75 min

Workup

  1. temperaturecooled
  2. customevaporated down
  3. additionThe residue is treated with petroleum ether/ethyl acetate 9:1 in the ultrasound bath
  4. filtrationfiltered
  5. customdried
  6. custom8.3 g (III-2) are obtained as a solid

Sources & evidence

ORD record
ord-cebebac7920d4db8ba1a5243b0eba835
Source dataset
uspto-grants-2015_08
Patent number
US09115142B2

Reaction notes

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