HCID 59239149, compound → (S)-5-(7-methyl-4-(3-methylmorpholino)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)thiazol-2-amine

HRID 1626617Notes

Reaction equation

HRID 1626617 reaction equation
C(NC(=O)NC1C=C[C:9]([C:12]2[N:13]=[C:14]([N:29]3[CH2:34][CH2:33][O:32][CH2:31][C@@H:30]3[CH3:35])[C:15]3[CH2:21][CH2:20][N:19]([C:22](OC(C)(C)C)=O)[CH2:18][C:16]=3[N:17]=2)=CC=1)C.CC1(C)C(C)(C)OB(C2[S:49][C:48]([NH:50]C(=O)OC(C)(C)C)=[N:47][CH:46]=2)O1.ClC1N=C(N2CCOC[C@@H]2C)C2CCN(C)CC=2N=1>>[CH3:22][N:19]1[CH2:20][CH2:21][C:15]2[C:14]([N:29]3[CH2:34][CH2:33][O:32][CH2:31][C@@H:30]3[CH3:35])=[N:13][C:12]([C:9]3[S:49][C:48]([NH2:50])=[N:47][CH:46]=3)=[N:17][C:16]=2[CH2:18]1

Participants

4

Reactant 3

HCID 59239149HCID 59239149, compoundHCID 72210849tert-butyl N-(5-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-thiazol-2-yl)carbamateHCID 86663156(S)-4-(2-chloro-7-methyl-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4-yl)-3-methylmorpholine2×

Product 1

HCID 86663160(S)-5-(7-methyl-4-(3-methylmorpholino)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)thiazol-2-amine

Procedure

Method as described for intermediate 5 using tert-butyl (5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiazol-2-yl)carbamate and (S)-4-(2-chloro-7-methyl-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4-yl)-3-methylmorpholine (intermediate 13) as starting materials. The tert-butyl carboxylate group was removed under the reaction conditions. The mixture was concentrated in vacuo and purified by flash SCX2 chromatography affording (S)-5-(7-methyl-4-(3-methylmorpholino)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)thiazol-2-amine.

Workup

  1. customThe tert-butyl carboxylate group was removed under the reaction conditions
  2. concentrationThe mixture was concentrated in vacuo
  3. custompurified by flash SCX2 chromatography

Sources & evidence

ORD record
ord-fb5a2afbc5a84fcd9a7d0c69cfecaec7
Source dataset
uspto-grants-2014_07
Patent number
US08785457B2

Reaction notes

Loading…