Ammonia → HCID 54741086, compound

HRID 420443Notes

Reaction equation

HRID 420443 reaction equation
[OH:1][C:2]1[C:11]2[CH:10]=[N:9][C:8]([O:12][CH3:13])=[N:7][C:6]=2[N:5]([CH3:14])[C:4](=[O:15])[C:3]=1[C:16]([NH:18][CH2:19][C:20]([O:22]C(C)(C)C)=[O:21])=[O:17].OC1C2C=NC(S(C)(=O)=O)=NC=2N(C)C(=O)C=1C(NCC(OC(C)(C)C)=O)=O.N.CO>C1COCC1>[OH:1][C:2]1[C:11]2[CH:10]=[N:9][C:8]([O:12][CH3:13])=[N:7][C:6]=2[N:5]([CH3:14])[C:4](=[O:15])[C:3]=1[C:16]([NH:18][CH2:19][C:20]([OH:22])=[O:21])=[O:17]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 887MethanolHCID 66658633HCID 66658633, compoundHCID 66658634HCID 66658634, compound

Product 1

HCID 54741086HCID 54741086, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

tert-Butyl 2-(5-hydroxy-2-methoxy-8-methyl-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidine-6-carboxamido)acetate. To a mixture of tert-butyl 2-(5-hydroxy-8-methyl-2-(methylsulfonyl)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidine-6-carboxamido)acetate (141 mg, 0.34 mmol) and THF (10 mL) was added ammonia, 2.0M methyl alcohol (3 mL, 5.1 mmol) at 0° C. under N2. The mixture was then stirred at 0° C. and warmed to room temperature overnight. LCMS showed no starting material was left and two peaks corresponding to the 7-amino and to the 7-OMe product (ca. 1:1). The white solid was filtered off and discarded. The filtrate was concentrated under reduced pressure to give the title compound. MS m/z: Calculated: 364.35. Observed: 365.

Workup

  1. temperaturewarmed to room temperature overnight
  2. waitwas left
  3. filtrationThe white solid was filtered off
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c77d540f9a534d179535516e4228f58b
Source dataset
uspto-grants-2012_01
Patent number
US08097620B2

Reaction notes

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