Diisopropylethylamine → HCID 178494310, compound

HRID 928174Notes

Reaction equation

HRID 928174 reaction equation
Cl[C:2]1[N:10]=[C:9]([F:11])[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][NH:6]2.Cl.[CH3:13][O:14][C:15]1[C:19]([NH2:20])=[CH:18][N:17]([CH3:21])[N:16]=1.C(N(CC)C(C)C)(C)C>CS(C)=O>[F:11][C:9]1[N:8]=[C:7]2[C:3]([N:4]=[CH:5][NH:6]2)=[C:2]([NH:20][C:19]2[C:15]([O:14][CH3:13])=[N:16][N:17]([CH3:21])[CH:18]=2)[N:10]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 755257993-methoxy-1-methyl-1H-pyrazol-4-amine hydrochlorideHCID 178506011HCID 178506011, compound

Product 1

HCID 178494310HCID 178494310, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A suspension of 6-chloro-2-fluoro-9H-purine (5.49 g, 31.8 mmol, 1.00 eq), 3-methoxy-1-methyl-1H-pyrazol-4-amine hydrochloride (6.60 g, 40.34 mmol, 1.26 eq), and N,N-diisopropylethylamine (16.6 mL, 95.5 mmol, 3.00 eq) in DMSO (31.8 mL) was stirred at ambient temperature for 19 hr. The reaction mixture was then concentrated in vacuo at 50° C., poured into water (250 mL), and stirred vigorously at 0° C. for 1 hr. The resulting solids were filtered off, washed with ice cold water (20 mL), and dried for 16 hr at 50° C. to give the title compound (7.26 g, 87% yield, 96% purity) as a light yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 13.03 (br. s., 1 H) 9.21 (br. s., 1 H) 8.18 (br. s., 1 H) 7.74 (br. s., 1 H) 3.81 (br. s., 3 H) 3.71 (s, 3H). m/z (APCI+) for C10H11FN7O 264.2 (M+H)+.

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo at 50° C.
  2. additionpoured into water (250 mL)
  3. stirringstirred vigorously at 0° C. for 1 hr
  4. filtrationThe resulting solids were filtered off
  5. washwashed with ice cold water (20 mL)
  6. customdried for 16 hr at 50° C.

Sources & evidence

ORD record
ord-4c61adb23fe44a81a6e5412f07f0664c
Source dataset
uspto-grants-2016_03
Patent number
US09290496B2

Reaction notes

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