Dichloromethane → HCID 118599058, compound

HRID 1050388Notes

Reaction equation

HRID 1050388 reaction equation
C(OC([N:8]([C:16]1[C:21]([O:22]C)=[C:20]([NH:24][C:25]2[C:30](=[O:31])[N:29]3[C:32]4([CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]4)[NH:33][C:34](=[O:35])[C:28]3=[C:27]([CH3:41])[CH:26]=2)[N:19]=[CH:18][N:17]=1)C(=O)OC(C)(C)C)=O)(C)(C)C.ClCCl.B(Br)(Br)Br>O>[NH2:8][C:16]1[N:17]=[CH:18][N:19]=[C:20]([NH:24][C:25]2[C:30](=[O:31])[N:29]3[C:32]4([CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]4)[NH:33][C:34](=[O:35])[C:28]3=[C:27]([CH3:41])[CH:26]=2)[C:21]=1[OH:22]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 25134Boron tribromideHCID 118598639HCID 118598639, compound

Product 1

HCID 118599058HCID 118599058, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A flask was charged with tert-butyl N-tert-butoxycarbonyl-N-(5-methoxy-6-((8′-methyl-1′,5′-dioxo-1′,5′-dihydro-2′H-spiro[cyclohexane-1,3′-imidazo[1,5-a]pyridin]-6′-yl)amino)pyrimidin-4-yl)carbamate (3, 0.40 g, 0.70 mmol) and dichloromethane (20 mL) was added and mixture was cooled to −20° C. boron tribromide (0.87 g, 3.50 mmol) was then added to the mixture drop wise. The reaction mass was stirred at room temperature overnight. After completion, water was added to the reaction mixture and quenched with saturated aqueous solution of sodium bicarbonate till pH 8. Yellow solid was precipitated out, filtered and washed with water (20 mL) followed by diethyl ether then finally dried under high vacuum to afford 6′-((6-amino-5-hydroxypyrimidin-4-yl)amino)-8′-methyl-2′H-spiro[cyclohexane-1,3′-imidazo[1,5-a]pyridine]-1′,5′-dione (Cpd. No. 202) as yellow solid. Yield: 0.085 g, 34%; MS (ESI) m/z 357.16 [M+1]+; 1H NMR: (400 MHz, DMSO-d6) δ 10.06 (s, 1H), 9.15 (brs, 1H), 8.50 (s, 1H), 8.40 (m, 1H), 8.08 (s, 1H), 6.65 (brs, 2H), 3.00-2.94 (m, 2H), 2.44 (s, 3H), 1.73-1.62 (m, 5H), 1.46-1.43 (m, 2H), 1.24-1.21 (m, 1H).

Workup

  1. additionwas added
  2. additionwas then added to the mixture drop wise
  3. customquenched with saturated aqueous solution of sodium bicarbonate till pH 8
  4. customYellow solid was precipitated out
  5. filtrationfiltered
  6. washwashed with water (20 mL)
  7. customthen finally dried under high vacuum

Sources & evidence

ORD record
ord-947e865eee514b67a9b93511c965238c
Source dataset
uspto-grants-2016_07
Patent number
US09382248B2

Reaction notes

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