HCID 13557967, compound → HCID 58034294, compound

HRID 1914853Notes

Reaction equation

HRID 1914853 reaction equation
[NH2:1][C:2]1[N:7]2[N:8]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:10]=[C:6]2[N:5]=[CH:4][C:3]=1[C:15](OCC)=[O:16]>O1CCCC1>[NH2:1][C:2]1[N:7]2[N:8]=[C:9]([C:11]([CH3:12])([CH3:14])[CH3:13])[CH:10]=[C:6]2[N:5]=[CH:4][C:3]=1[CH2:15][OH:16]

Participants

3

Reactant 1

HCID 13557967HCID 13557967, compound

Product 1

HCID 58034294HCID 58034294, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
25 °C

Procedure

A solution of ethyl 7-amino-2-tert-butylpyrazolo[1,5-a]pyrimidine-6-carboxylate (740 mg, 2.82 mmol, 1.00 equiv) in tetrahydrofuran (12 mL) was added dropwise LiBHEt3 (8.5 mL of a 1 M solution in THF, 3.0 eq.) at 0° C. under nitrogen. After addition, the resulting solution was stirred for 4 h at 25° C. Additional LiBHEt3 (0.85 mL of a 1 M solution in THF, 0.85 mmol, 0.3 eq.) was added and the mixture was stirred for another 1 h. After a total of 3 h, the reaction was then quenched with water and extracted with ethyl acetate (100 mL×3). The organic layers were combined, dried and concentrated. The residue was loaded onto a silica gel column with CH2Cl2/MeOH (30:1) as an eluent to give Compound [CCXXXVI] as a white solid: LCMS (m/e) 221 (M+H); 1H NMR (300 MHz, DMSO-d6) δ ppm 8.02 (s, 1H), 7.32 (s, 2H), 6.22 (s, 1H), 4.94 (t, J=5.7 Hz, 1H), 4.53 (d, J=5.7 Hz, 2H), 1.36 (s, 9H).

Workup

  1. additionAfter addition
  2. stirringthe mixture was stirred for another 1 h
  3. customAfter a total of 3 h, the reaction was then quenched with water
  4. extractionextracted with ethyl acetate (100 mL×3)
  5. customdried
  6. concentrationconcentrated
  7. customto give Compound [CCXXXVI] as a white solid

Sources & evidence

ORD record
ord-b260863432e9499aa727888d904480de
Source dataset
uspto-grants-2013_12
Patent number
US08614221B2

Reaction notes

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